FORMAL TOTAL SYNTHESIS OF FK506 - CONCISE CONSTRUCTION OF THE C(10)-C(34) SEGMENT VIA AN EFFECTIVE COUPLING TACTIC

被引：29

作者：

SMITH, AB ^{[1
]}

CHEN, KM ^{[1
]}

ROBINSON, DJ ^{[1
]}

LAAKSO, LM ^{[1
]}

HALE, KJ ^{[1
]}

机构：

[1] UNIV PENN,MONELL CHEM SENSES CTR,PHILADELPHIA,PA 19104

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 25期

关键词：

D O I：

10.1016/S0040-4039(00)73331-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal total synthesis of the potent immunosuppressant FK506 (1) has been achieved via a concise construction of the Merck advanced intermediate (-)-2. Key features of the successful strategy include stereocontrolled sigma-bond installation of the trisubstituted olefin moieties and an efficient coupling of the C(24)-C(34) dithiane (-)-10 with the C(10)-C(23) alpha-silyloxy primary iodide (-)-9.

引用

页码：4271 / 4274

页数：4

共 50 条

[1] SYNTHESIS OF THE C-10-C-34 SEGMENT OF THE IMMUNOSUPPRESSANT FK506
GU, RL
SIH, CJ
TETRAHEDRON LETTERS, 1990, 31 (23) : 3287 - 3290
[2] AN ENANTIOSELECTIVE SYNTHESIS OF THE C(10) TO C(20) FRAGMENT OF FK506
MAIER, ME
SCHOFFLING, B
TETRAHEDRON LETTERS, 1991, 32 (01) : 53 - 56
[3] A SYNTHESIS OF THE C24-C34 SEGMENT OF FK-506
KOCIENSKI, P
STOCKS, M
DONALD, D
PERRY, M
SYNLETT, 1990, (01) : 38 - 39
[4] A STEREOSELECTIVE AND CONVERGENT SYNTHESIS OF A C21-C34 FRAGMENT OF FK506
MAIER, ME
HALLER, BU
STUMPF, R
FISCHER, H
SYNLETT, 1993, (11) : 863 - 865
[5] TOTAL SYNTHESIS OF FK506 AND AN FKBP PROBE REAGENT, (C8,C9-(C-13)2)-FK506
NAKATSUKA, M
RAGAN, JA
SAMMAKIA, T
SMITH, DB
UEHLING, DE
SCHREIBER, SL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) : 5583 - 5601
[6] A CHEMOENZYMATIC SYNTHESIS OF THE C-10-C-19 MOIETY OF FK506
GU, RL
SIH, CJ
TETRAHEDRON LETTERS, 1990, 31 (23) : 3283 - 3286
[7] Total synthesis of FK-506 .1. Construction of the C16-C34 fragment
Ireland, RE
Liu, LB
Roper, TD
TETRAHEDRON, 1997, 53 (39) : 13221 - 13256
[8] AN ENANTIOSELECTIVE SYNTHESIS OF THE C(10) TO C(23) BACKBONE OF THE POTENT IMMUNOSUPPRESSANT FK506
SMITH, AB
HALE, KJ
TETRAHEDRON LETTERS, 1989, 30 (09) : 1037 - 1040
[9] AN ENANTIOSELECTIVE SYNTHESIS OF THE C(10) TO C(23) BACKBONE OF THE POTENT IMMUNOSUPPRESSANT FK506
SMITH, AB
HALE, KJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 197 : 64 - ORGN
[10] SYNTHESIS OF THE C20-C34 SEGMENT OF THE IMMUNOSUPPRESSANT FK-506 VIA STEREOCONTROLLED ALDOL COUPLING - APPLICATION OF A REMOTE CHELATION EFFECT
WHITE, JD
TOSKE, SG
YAKURA, T
SYNLETT, 1994, (08) : 591 - 593

← 1 2 3 4 5 →