Isolation and Synthesis of Azuriaplysins A and B, Bromoditerpenes with an a-Methylene Carbonyl from the Sea Hare Aplysia kurodai

被引：11

作者：

Ohyoshi, Takayuki ^{[1
]}

Zhao, Yiwen ^{[1
]}

Kigoshi, Hideo ^{[1
]}

机构：

[1] Univ Tsukuba, Fac Pure & Appl Sci, Dept Chem, Tsukuba 3058571, Japan

来源：

JOURNAL OF NATURAL PRODUCTS | 2022年 / 85卷 / 08期

关键词：

MARINE; ISOCONCINNDIOL; APLYRONINE;

D O I：

10.1021/acs.jnatprod.2c00476

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

New bromoditerpenes having an alpha-methylene carbonyl structure, azuriaplysins A (1) and B (2), were isolated from the sea hare Aplysia kurodai. Their relative stereostructures were determined based on one-and two-dimensional NMR spectroscopic analysis. In addition, the absolute stereostructures were determined by the total synthesis of both enantiomers of azuriaplysins A (1) and B (2), the key points of which were bromocyclization of farnesol and optical resolution of a key intermediate. Azuriaplysin B (2) and its enantiomer exhibited moderate cytotoxicity against HeLa S3 cells.

引用

页码：2082 / 2089

页数：8

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