Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3420-3425.DOI: 10.6023/cjoc202005058 Previous Articles     Next Articles

15-Oxopuupehenoic Acid可能结构1b的不对称全合成

宋华月, 刘霖, 谢新刚   

  1. 兰州大学化学化工学院 功能有机分子化学国家重点实验室 兰州 730000
  • 收稿日期:2020-05-22 修回日期:2020-05-29 发布日期:2020-06-10
  • 通讯作者: 谢新刚
  • 基金资助:

Asymmetric Total Synthesis of the Possible Structure 1b of 15-Oxopuupehenoic Acid

Song Huayue, Liu Lin, Xie Xingang   

  1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000
  • Received:2020-05-22 Revised:2020-05-29 Published:2020-06-10
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21472079).

15-Oxopuupehenoic acid is a new merosesquiterpenoid isolated in 2009 by Crews group from the crude sponge extracts prioritized a Papua New Guinea collection of Hyrtios sp. Its possible structure was deduced to be tetracyclic chromanones 1a~1b or benzo[c]oxepin-1(3H)-ones 1c~1d based on the spectra data, and later determinded to be 1a by analysis of its gHMBC correlations spectra. Recently Alvarez-Manzaneda and Chahboun group obtained 1a by chemical synthesis which spectra data did not match well with those of natural 15-oxopuupehenoic acid. We started from R-(-)-carvone and approched its possible structure 1b through a convergent coupling-cyclization strategy. Our sythesis featured Suzuki carbonylative coupling reaction and KOH promoted intramolecular cyclization reaction to construct the unique chromanone subunit. The spectra data of synthetic 1b did not match well with those of natural 15-oxopuupehenoic acid either which indicated its structure needed revision.

Key words: 15-oxopuupehenoic acid, Suzuki carbonylative coupling, KOH promotion, intramolecular cyclization, chromanone