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
收藏
页码：2050 / 2053
页数：4
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