天然产物Cyanolide A和Cocosolide的合成研究进展

doi:10.6023/cjoc201904071

摘要/Abstract

Cyanolide A和cocosolide是两个结构高度相似的具有对称结构的十六元内酯天然产物.Cyanolide A是从巴布亚新几内亚的Lyngbya bouillonii提取物中分离得到，具有良好的灭螺效果，可以有效阻断血吸虫病的传播，而cocosolide则是从关岛附近的金黄色的蓝藻提取物中分离.它们新颖的结构和良好的生理活性引起众多化学家的关注.根据氧杂迈克尔加成反应、氧鎓离子环化反应和过渡金属催化环化反应等四氢吡喃环构筑方法，综述了cyanolide A和cocosolide的合成工作.

关键词: Cyanolide A, Cocosolide, 全合成, 氧杂迈克尔加成, 氧鎓离子环化反应, 过渡金属催化的环化反应

Cyanolide A and cocosolide, two 16-membered dimeric macrolide xylopyranosides, were isolated from Guam and Papua New Guinea, respectively. Their fascinating structures and outstanding biological activities had attracted great attentions from chemists. The synthesis of cyanolide A and cocosolide is reviewed based on the construction methods of tetrahydropyran ring, which involves oxo-Michael addition reaction, oxo-carbenium cyclization and transition-metal catalyzed cyclization reactions.

Key words: cyanolide A, cocosolide, total synthesis, oxo-Michael addition, oxo-carbenium cyclization reaction, transition-metal catalyzed cyclization reaction

引用此文

张榴, 张梦帆, 齐陈泽, 杨震. 天然产物Cyanolide A和Cocosolide的合成研究进展[J]. 有机化学, 2019, 39(11): 3105-3113.

Zhang Liu, Zhang Mengfan, Qi Chenze, Yang Zhen. Synthetic Studies toward Natural Occurred Cyanolide A and Cocosolide[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3105-3113.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 14

图 1. Cyanolide A和cocosolide的结构

Figure 1. Structures of cyanolide A and cocosolide

图式 1. Hong小组cyanolide A首次全合成

Scheme 1. Hong's first total synthesis of cyanolide A

图式 2. Reddy小组cyanolide A双内酯大环骨架的合成

Scheme 2. Reddy's synthesis of cyanolide A aglycone

图式 3. Pabbaraja小组cyanolide A双内酯大环骨架的合成

Scheme 3. Pabbaraja's synthesis of cyanolide A aglycone

图式 4. Krische小组cyanolide A的全合成

Scheme 4. Krische's total synthesis of cyanolide A

图式 5. Bates小组cyanolide A的全合成

Scheme 5. Bates's total synthesis of cyanolide A

图式 6. Zhou小组cyanolide A双内酯大环骨架的合成

Scheme 6. Zhou's synthesis of cyanolide A aglycone

图式 7. Rychnovsky第一代cyanolide A双内酯大环骨架的合成

Scheme 7. Rychnovsky's first generation synthesis of cyanolide A aglycone

图式 8. Jennings小组cyanolide A双内酯大环骨架的合成

Scheme 8. Jennings's synthesis of cyanolide A aglycone

图式 9. Rychnovsky’s第二代cyanolide A全合成

Scheme 9. Rychnovsky's second generation synthesis of cyanolide A

图式 10. She小组cyanolide A的全合成

Scheme 10. She's total synthesis of cyanolide A

图式 11. Ye小组cocosolide的全合成.

Scheme 11. Ye's total synthesis of cocosolide

图式 12. Cyanolide A (1)和cocosolide (2)的合成

Scheme 12. Synthesis of cyanolide A (1) and cocosolide (2)

图式 13. Cocosolide (2)的合成路线设计

Scheme 13. Synthetic plan for cocosolide (2)

参考文献 44

[1]	Newman D. J. Cragg G. M. J. Nat. Prod. 2016 79 629. doi: 10.1021/acs.jnatprod.5b01055
[2]	Giordanetto F. Kihlberg J. J. Med. Chem. 2014 57 278. doi: 10.1021/jm400887j
[3]	McGuire J. M. Bunch R. L. Anderson R. C. Boaz H. E. Flynn E. H. Powell H. M. Smith J. W. Antibiot. Chemother. 1952 2 281.
[4]	Altmann K.-H. Gaugaz F. Z. Schiess R. Mol. Diversity 2011 15 383. doi: 10.1007/s11030-010-9291-0
[5]	Seiple I. B. Zhang Z. Y. Jakubec P. Langlois-Mercier A. Wright P. M. Hog D. T. Yabu K. Z. Allu S. R. Fukuzaki T. Carlsen P. N. Kitamura Y. Zhou X. Condakes M. L. Szczypiński F. T. Green W. D. Myers A. G. Nature 2016 533 338. doi: 10.1038/nature17967
[6]	Pereira A. R. McCue C. F. Gerwick W. H. J. Nat. Prod. 2010 73 217. doi: 10.1021/np9008128
[7]	Gunaseker S. P. Li Y. Ratnayake R. Luo D. M. Lo J. Reibenspies J. H. Xu Z. S. Clare-Salzler M. J. Ye T. Paul V. J. Luesch H. Chem.-Eur. J. 2016 22 8158. doi: 10.1002/chem.201600674
[8]	Rao R. M. Faulkner D. J. J. Nat. Prod. 2002 65 386. doi: 10.1021/np010495l
[9]	Steinmann P. Keiser J. Bos R. Tanner M. Utzinger J. Lancet. Infect. Dis. 2006 6 411. doi: 10.1016/S1473-3099(06)70521-7
[10]	Chitsulo L. Engels D. Montresor A. Savioli L. Acta Trop. 2000 77 41. doi: 10.1016/S0001-706X(00)00122-4
[11]	World Health Organization Report of the Scientific Working Group Meeting on Schistosomiasis, Geneva, Switzerland, November 14~16, 2005.
[12]	(a) Hong, J.; Kim, H. Org. Lett. 2010, 12, 2880. doi: 10.1021/ol101022z
	(b) Hajare, A. K.; Ravikumar, V.; Khaleel, S.; Bhuniya, D.; Reddy, D. S. J. Org. Chem. 2011, 76, 963. doi: 10.1021/ol101022z
	(c) Yang, Z.; Xie, X.; Jing, P.; Zhao, G.; Zheng, J.; Zhao, C.; She, X. Org. Biomol. Chem. 2011, 9, 984. doi: 10.1021/ol101022z
	(d) Pabbaraja, S.; Satyanarayana, K.; Ganganna, B.; Yadav, J. S. J. Org. Chem. 2011, 76, 1922. doi: 10.1021/ol101022z
	(e) Gesinski, M. R.; Rychnovsky, S. D. J. Am. Chem. Soc. 2011, 133, 9727. doi: 10.1021/ol101022z
	(f) Sharpe, R. J.; Jennings, M. P. J. Org. Chem. 2011, 76, 8027. doi: 10.1021/ol101022z
	(g) Tay, G. C.; Gesinski, M. R.; Rychnovsky, S. D. Org. Lett. 2013, 15, 4536. doi: 10.1021/ol101022z
	(h) Waldeck, A. R.; Krische, M. J. Angew. Chem., Int. Ed. 2013, 52, 4470. doi: 10.1021/ol101022z
	(i) Bates, R. W.; Lek, T. G. Synthesis 2014, 46, 1731. doi: 10.1021/ol101022z
	(j) Che, W.; Li, Y. Z.; Liu, J. C.; Zhu, S. F.; Xie, J. H.; Zhou, Q. L. Org. Lett. 2019, 21, 2369. doi: 10.1021/ol101022z
	(j) Lee, K.; Lanier, M. L.; Kwak, J. H.; Kim, H.; Hong, J. Y. Nat. Prod. Rep. 2016, 33, 1393. doi: 10.1021/ol101022z
[13]	(a) Ye, T.; Xu, Z.; Li, Y.; Luesch, H.; Paul, V. J.; Gunasekera, S. P. CN 105884843, 2016.
	(b) Luesch, H.; Paul, V. J.; Gunasekera, S. WO 2017152099, 2017.
[14]	Armesto D. Horspool W. M. Gallego M. G. Agarrabeitia A. R. J. Chem. Soc., Perkin Trans. 1 1992 163.
[15]	Mohapatra D. K. Das P. P. Reddy D. S. Yadav J. S. Tetrahedron Lett. 2009 50 5941. doi: 10.1016/j.tetlet.2009.08.028
[16]	Barry C. S. Bushby N. Charmant J. P. H. Elsworth J. D. Harding J. R. Willis C. L. Chem. Commun. 2005 5097.
[17]	(a) Nugent, W. A. Chem. Commun. 1999, 1369. doi: 10.1021/ja027271p
	(b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. doi: 10.1021/ja027271p
[18]	Shiina I. Kubota M. Oshiumi H. Hashizume M. J. Org. Chem. 2004 69 1822. doi: 10.1021/jo030367x
[19]	Ball M. Baron A. Bradshaw B. Omori H. MacCormick S. Thomas E. J. Tetrahedron Lett. 2004 45 8737. doi: 10.1016/j.tetlet.2004.09.124
[20]	Liu J. Yang J. H. Ko C. Hsung R. P. Tetrahedron Lett. 2006 47 6121. doi: 10.1016/j.tetlet.2006.06.067
[21]	Inanaga J. Hirata K. Saeki H. Katsuki T. Yamaguchi M. Bull. Chem. Soc. Jpn. 1979 52 1989. doi: 10.1246/bcsj.52.1989
[22]	Crimmins M. T. Emmitte K. A. Org. Lett. 1999 1 2029. doi: 10.1021/ol991201e
[23]	Corey E. J. Bakshi R. K. Shibata S. J. Am. Chem. Soc. 1987 109 5551. doi: 10.1021/ja00252a056
[24]	(a) Bower, J. F.; Kim, I. S.; Patman, R. L.; Krische, M. J. Angew. Chem., Int. Ed. 2008, 48, 34. doi: 10.1002/anie.200802938
	(b) Patman, R. L.; Bower, J. F.; Kim, I. S.; Krische, M. J. Aldrichim. Acta 2008, 41, 95. doi: 10.1002/anie.200802938
	(c) Han, S. B.; Kim, I. S.; Krische, M. J. Chem. Commun. 2009, 7278. doi: 10.1002/anie.200802938
[25]	Fuwa H. Noto K. Sasaki M. Org. Lett. 2011 13 1820. doi: 10.1021/ol200333p
[26]	Fuwa H. Heterocycles 2012 85 1255. doi: 10.3987/REV-12-730
[27]	Pirrung M. C. Kenney P. M. J. Org. Chem. 1987 52 2335. doi: 10.1021/jo00387a053
[28]	(a) Che, W.; Wen, D. C.; Zhu, S. F.; Zhou, Q. L. Org. Lett. 2018, 20, 3305. doi: 10.1021/acs.orglett.8b01193
	(b) Bao, D. H.; Wu, H. L.; Liu, C.-L.; Xie, J. H.; Zhou, Q. L. Angew. Chem., Int. Ed. 2015, 54, 8791. doi: 10.1021/acs.orglett.8b01193
[29]	Sun J. Dong Y. Cao L. Wang X. Wang S. Hu Y. J. Org. Chem. 2004 69 8932. doi: 10.1021/jo0486239
[30]	Schaus S. E. Brandes B. D. Larrow J. F. Tokunaga M. Hansen K. B. Gould A. E. Furrow M. E. Jacobsen E. N. J. Am. Chem. Soc. 2002 124 1307. doi: 10.1021/ja016737l
[31]	Nicolaou K. C. Li A. Edmonds D. J. Tria S. Ellery S. P. J. Am. Chem. Soc. 2009 131 16905. doi: 10.1021/ja9068003
[32]	Zhang Y. Sammakia T. J. Org. Chem. 2006 71 6262. doi: 10.1021/jo0605694
[33]	VanRheenen V. Kelly R. C. Cha D. Y. Tetrahedron Lett. 1976 17 1973. doi: 10.1016/S0040-4039(00)78093-2
[34]	(a) Evans, D. A.; Gauchet-Prunet, J. A. J. Org. Chem., 1993, 58, 2446. doi: 10.1021/jo00061a018
	(b) Rotulo-Sims, D.; Prunet, J. Org. Lett. 2007, 9, 4147 doi: 10.1021/jo00061a018
[35]	Evans D. A. Dart M. J. Duffy J. L. Yang M. G. J. Am. Chem. Soc. 1996 118 4322. doi: 10.1021/ja953901u
[36]	Narasaka K. Pai F. C. Tetrahedron 1984 40 2233. doi: 10.1016/0040-4020(84)80006-X
[37]	Evans D. A. Hoveyda A. H. J. Am. Chem. Soc. 1990 112 6447. doi: 10.1021/ja00173a071
[38]	Petrier C. Luche J. L. J. Org. Chem. 1985 50 910. doi: 10.1021/jo00206a047
[39]	White J. D. Hong J. Robarge L. A. Tetrahedron Lett. 1999 40 1463. doi: 10.1016/S0040-4039(98)02693-8
[40]	Gao D. O'Doherty G. A. J. Org. Chem. 2005 70 9932. doi: 10.1021/jo051681p
[41]	Reiff E. A. Nair S. K. Henri J. T. Greiner J. F. Reddy B. S. Chakrasali R. David S. A. Chiu T.-L. Amin E. A. Himes R. H. Vander Velde D. G. Georg G. I. J. Org. Chem. 2010 75 86. doi: 10.1021/jo901752v
[42]	(a) Armstrong, A.; Scutt, J. N. Org. Lett. 2003, 5, 2331. doi: 10.1021/ol0346887
	(b) Armstrong, A.; Scutt, J. N. Chem. Commun. 2004, 510. doi: 10.1021/ol0346887
	(c) Delhaye, L.; Merschaert, A.; Delbeke, P.; Briúne, W. Org. Process Res. Dev. 2007, 11, 689. doi: 10.1021/ol0346887
	(d) Bray, C. D.; Minicone, F. Chem. Commun. 2010, 46, 5867. doi: 10.1021/ol0346887
	(e) Kumar, P.; Dubey, A.; Harbindu, A. Org. Biomol. Chem. 2012, 10, 6987. doi: 10.1021/ol0346887
[43]	(a) Ren, R. G.; Mao, Z. Y.; Wei, B. G.; Lin, G. G. Chin. J. Org. Chem. 2015, 35, 2313 (in Chinese). doi: 10.6023/cjoc201507033
	(任荣国, 毛卓亚, 魏邦国, 林国强, 有机化学, 2015, 35, 2313.) doi: 10.6023/cjoc201507033
	(b) Yu, J. F.; Feng, R. K.; Yang, Z. Chin. J. Org. Chem. 2017, 37, 2526 (in Chinese). doi: 10.6023/cjoc201507033
	(于江帆, 冯若昆, 杨震, 有机化学, 2017, 37, 2526. doi: 10.6023/cjoc201507033
[44]	Shi D. X. Feng X. Zhuang X. L. Chai H. X. Liu T. Zhang Q. Li J. R. Chin. J. Org. Chem. 2014 34 2543. doi: 10.6023/cjoc201405007
	史大昕冯雪庄晓磊柴洪新刘霆张奇李加荣有机化学 2014 34 2543. doi: 10.6023/cjoc201405007