Synthetic approaches to Rapamycin: Synthesis of a C10-C26 fragment via a one-pot Julia olefination reaction

被引：0

作者：

Bellingham, R ^{[1
]}

Jarowicki, K ^{[1
]}

Kocienski, P ^{[1
]}

Martin, V ^{[1
]}

机构：

[1] UNIV SOUTHAMPTON,DEPT CHEM,SOUTHAMPTON SO17 1BJ,HANTS,ENGLAND

来源：

SYNTHESIS-STUTTGART | 1996年 / 02期

关键词：

Rapamycin; immunosuppressant; ketenedithioacetal; triene 1,4-asymmetric induction; Julia olefination;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Keys steps in a synthesis of the C10-C26 fragment of the immunosuppressant Rapamycin include (a) the use of a metallated benzothiazolyl sulfone in a one-pot Julia olefination to create the C21-C22 alkene stereoselectively and (b) a diastereoselective acid-catalysed cyclisation of a hydroxyl function onto a ketenedithioacetal (1,4-asymmetric induction) in order to create the oxane ring and fix the stereochemistry at C11.

引用

页码：285 / &

页数：13

共 5 条

[1] Synthetic approaches to rapamycin .3. Synthesis of a C1-C21 fragment
Harris, L
Jarowicki, K
Kocienski, P
SYNLETT, 1996, (09) : 903 - &
[2] Synthetic approaches to rapamycin .2. A synthesis of a C21-C42 fragment
Norley, M
Kocienski, P
Faller, A
SYNLETT, 1996, (09) : 900 - &
[3] A SYNTHETIC APPROACH TO THE C26-C32 FRAGMENT OF RAPAMYCIN - A SYNTHESIS OF ALLYLIC ALCOHOLS FROM ALLYLIC FURYLSILANES
NORLEY, MC
KOCIENSKI, PJ
FALLER, A
SYNLETT, 1994, (01) : 77 - 78
[4] SYNTHETIC STUDIES TOWARDS THE IMMUNOSUPPRESSANT FK-506 SYNTHESIS OF THE C-10-C-34 FRAGMENT
WANG, ZY
TETRAHEDRON LETTERS, 1991, 32 (36) : 4631 - 4634
[5] Convenient synthesis of perfluoroalkyl substituted 2-oxopyridine-fused 1,3-diazaheterocycles via a one-pot three-component reaction
Wang, Zewei
Sun, Tianqi
Chen, Jie
Deng, Hongmei
Shao, Min
Zhang, Hui
Cao, Weiguo
TETRAHEDRON, 2013, 69 (21) : 4270 - 4275

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