Construction of a pentacyclic ring system of isoryanodane diterpenoids by SmI2-mediated transannular cyclization

被引：8

作者：

Koshimizu, Masaki ^{[1
]}

Nagatomo, Masanori ^{[1
]}

Inoue, Masayuki ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 2018年 / 74卷 / 26期

关键词：

Isoryanodane diterpenoids; Natural product synthesis; Oxy-Cope rearrangement; Transannular cyclization; SmI2; DENSITY FUNCTIONALS; NATURAL-PRODUCTS; RYANODOL; (+)-RYANODINE; CHEMISTRY; ALPHA;

D O I：

10.1016/j.tet.2018.03.061

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isoryanodane diterpenoids possess a densely oxygenated and intricately fused pentacycle (ABCDE-ring), although its unique ring system has not yet been assembled chemically. The 6/5/7-membered BCD-rings of isoryanodanes differ from the 5/6/6-membered rings of the structurally-related ryanodanes. We previously achieved the total synthesis of ryanodine and five other ryanodane diterpenoids by employing the common ABDE-tetracyclic intermediate 1. Herein, we report a new strategy for constructing isoryanodane ABCDE-ring structure 3 from 1 via a combination of the oxy-Cope rearrangement and SmI2-mediated transannular cyclization. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：3384 / 3390

页数：7

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