Stereoselective Total Synthesis of (3R,5R)-5-Hydroxy-de-O-methyllasiodiplodin via the Prins Cyclization

被引：11

作者：

Yadav, Jhillu S. ^{[1
]}

Thrimurtulu, N. ^{[1
]}

Rahman, Md. Ataur ^{[1
]}

Reddy, J. Satyanarayana ^{[1
]}

Prasad, A. R. ^{[1
]}

Reddy, B. V. Subba ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNTHESIS-STUTTGART | 2010年 / 21期

关键词：

Prins cyclization; ring-closing metathesis; esterification; reductive ring opening; lactone; RING-CLOSING-METATHESIS; REDUCTIVE CLEAVAGE SEQUENCE; FORMAL TOTAL-SYNTHESIS; LASIODIPLODIA-THEOBROMAE; DIASTEREOSELECTIVE SYNTHESIS; LEUCASCANDROLIDE-A; APICULAREN-A; PALLADIUM; PROTOCOL; (R)-(+)-LASIODIPLODIN;

D O I：

10.1055/s-0030-1258244

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical stereoselective total synthesis of (3R,5R)-5-hydroxy-de-O-methyllasiodiplodin has been accomplished via Prins cyclization. It exhibits potato microtuber inducing activity. The synthetic sequence involves Prins cyclization, reductive opening of the pyran ring, esterification, and ring-closing metathesis (RCM) as the key steps.

引用

页码：3657 / 3662

页数：6

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