Total Synthesis of (+)-Neopeltolide by the Macrocyclization/Transannular Pyran Cyclization Strategy

被引：12

作者：

Nakazato, Kazuki ^{[1
]}

Oda, Mami ^{[1
]}

Fuwa, Haruhiko ^{[1
]}

机构：

[1] Chuo Univ, Fac Sci & Engn, Dept Appl Chem, Tokyo 1128551, Japan

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 22期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; CROSS-COUPLING REACTIONS; FORMAL TOTAL-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; MACROLACTONE CORE; NEOPELTOLIDE; MACROLIDE; IDENTIFICATION;

D O I：

10.1021/acs.orglett.2c01429

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An 11-step synthesis of (+)-neopeltolide was developed. The C1-C7 carboxylic acid and the C8-C16 alcohol were prepared, each in six steps, from (R)- and (S)-epichlorohydrin, respectively. After esterification, our tandem macrocyclization/transannular pyran cyclization strategy was applied to a stereo-controlled construction of the neopeltolide macrolactone. The side chain was synthesized in six steps from ethyl 4-oxazolecarboxylate through palladium-catalyzed cross-couplings. A Mitsunobu reaction of the neopeltolide macrolactone and the side chain completed the synthesis.

引用

页码：4003 / 4008

页数：6

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