Synthetic Studies of Sarsolilide A--Construction of the 14-Membered Cembranoid Skeleton

Acta Chimica Sinica ›› 2004, Vol. 62 ›› Issue (8): 811-817. Previous Articles Next Articles

Sarsolilide A的合成研究——十四元碳环骨架的构建

段志勇, 张家仲, 许杏祥

中国科学院上海有机化学研究所, 上海, 200032

投稿日期:2003-03-06 修回日期:2003-12-28 发布日期:2014-02-18
通讯作者: 许可祥,E-mail:xuxx@mail.sioc.ac.cn E-mail:xuxx@mail.sioc.ac.cn

Synthetic Studies of Sarsolilide A--Construction of the 14-Membered Cembranoid Skeleton

DUAN Zhi-Yong, ZHANG Jia-Zhong, XU Xing-Xiang

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2003-03-06 Revised:2003-12-28 Published:2014-02-18

Abstract

In the total synthesis of Sarsolilide A as a target molecule, the precursors 11 and 18, which were synthesized from geraniol and isobutyraldehyde respectively, were condensed via intermolecular HWE reaction. And the dihydroxyl groups at 7-C and 8-C in compound 20 were regioselectively introduced by Sharpless AD reaction. Subsequent conventional transformations afforded the cyclization precursor 5. The construction of the 14-membered cembranoid carbon ring was realized by low valent titanium induced McMurry reaction, giving compound 23 as the key intermediate.

Key words: Sarsolilide A, McMurry coupling, HWE reaction, Sharpless asymmetric dihydroxylation, total synthesis

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DUAN Zhi-Yong, ZHANG Jia-Zhong, XU Xing-Xiang. Synthetic Studies of Sarsolilide A--Construction of the 14-Membered Cembranoid Skeleton[J]. Acta Chimica Sinica, 2004, 62(8): 811-817.

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Sarsolilide A的合成研究——十四元碳环骨架的构建

Synthetic Studies of Sarsolilide A--Construction of the 14-Membered Cembranoid Skeleton

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