Toward the total synthesis of scytophycins: Synthesis of the C7-C21 fragments of scytophycins A, B, and C

被引：1

作者：

Ohyoshi, Takayuki ^{[1
]}

Namiki, Mayu ^{[1
]}

Miyazaki, Yuto ^{[1
]}

Sato, Shusei ^{[1
]}

Noguchi, Tomonari ^{[1
]}

Kigoshi, Hideo ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2023年 / 114卷

关键词：

Scytophycins; Cytotoxic macrolide; Diversity-oriented synthesis; Epoxidation; 4-Reduction; CONJUGATE REDUCTION; C(1)-C(18) SEGMENT; COUPLING REACTION; CHLORIDE; AGENTS;

D O I：

10.1016/j.tetlet.2022.154250

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Scytophysins are cytotoxic macrolides with a 22-membered ring and are characterized by their strong cytotoxicities targeting cytoskeletal protein actin. Toward the comprehensive total synthesis of scytophycins, we have investigated the late-state functionalization using fragment compounds. We established stereoselective construction of the C7-C21 part in scytophycins A and B involving characteristic C16 epoxide by using Sharpless epoxidation. Although stereoselectivity remains unsatisfactory, reduction of the C16 exo-olefin for the synthesis of scytophycin C was achieved.(c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：5

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