Asymmetric Synthesis of (-)-Martinellic Acid

被引：39

作者：

Davies, Stephen G. ^{[1
]}

Fletcher, Ai M. ^{[1
]}

Lee, James A. ^{[1
]}

Lorkin, Thomas J. A. ^{[1
]}

Roberts, Paul M. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 08期

关键词：

CYCLIZATION-ELIMINATION REACTION; FORMAL TOTAL-SYNTHESIS; PURE LITHIUM AMIDES; CONJUGATE ADDITION; MARTINELLIC ACID; RADICAL-ADDITION; TRICYCLIC CORE; NUCLEOPHILIC-SUBSTITUTION; ALKALOIDS MARTINELLINE; CYCLOADDITION APPROACH;

D O I：

10.1021/ol4007508

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A high-yielding total asymmetric synthesis of (-)-martinellic acid is reported. The conjugate addition of lithium (R)-N-allyl-N-(alpha-methyl-4-methoxybenzyl)amide to tert-butyl (E)-3[2'-(N,N-diallylamino)-5'-bromophenyl]propenoate and alkylation of the resultant beta-amino ester have been used as the key steps to install the C(9b) and C(3a) stereogenic centers, respectively, and a highly diastereoselective Wittig reaction/intramolecular Michael addition was then used to create the C(4) stereogenic center within this tricyclic molecular architecture.

引用

页码：2050 / 2053

页数：4

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