Catalytic Asymmetric Synthesis of the C1-C15 Segment of Spirastrellolide A

被引:4
|
作者
Sahara, Yui [1 ]
Cui, Jin [1 ]
Furutachi, Makoto [1 ]
Chen, Jingbo [1 ]
Watanabe, Takumi [1 ]
Shibasaki, Masakatsu [1 ]
机构
[1] Inst Microbial Chem BIKAKEN, Shinagawa Ku, 3-14-23 Kamiosaki, Tokyo 1410021, Japan
来源
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 01期
关键词
spirastrellolide A; catalytic asymmetric synthesis; catalytic enantioselective thioamide-aldol reaction; natural product synthesis; PP2A inhibitor; F METHYL-ESTER; 2ND-GENERATION TOTAL-SYNTHESIS; PROTEIN PHOSPHATASE 2A; ANION RELAY CHEMISTRY; ALDOL REACTION; PART; FRAGMENT; SUBUNIT; (+)-SPIRASTRELLOLIDE; TRIOXADISPIROKETAL;
D O I
10.1055/s-0036-1588068
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic asymmetric synthesis of the C1-C15 fragment of spirastrellolide A, a naturally occurring PP2A inhibitor, was achieved. To construct the 1,3-polyol system in a stereodefined manner, we took advantage of an iterative aldol strategy comprising the catalytic asymmetric thioamide-aldol reaction, and a diastereoselective crotylation process. A potential segment for the total synthesis of spirastrellolide A was thus accessed through a 14-step procedure.
引用
收藏
页码:69 / 75
页数:7
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