A FORMAL SYNTHESIS OF FK-506 - EXPLORATION OF SOME ALTERNATIVES TO MACROLACTAMIZATION

被引：78

作者：

JONES, AB ^{[1
]}

VILLALOBOS, A ^{[1
]}

LINDE, RG ^{[1
]}

DANISHEFSKY, SJ ^{[1
]}

机构：

[1] YALE UNIV,DEPT CHEM,NEW HAVEN,CT 06511

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 09期

关键词：

D O I：

10.1021/jo00296a042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The coupling of the previously described subunits 2,3, and 4 is described. The C28-C27E-double bond is fashioned from a sulfurane induced dehydration of alcohol 11. The C19-C20 E-double bond was constructed via a modified Julia process culminating in a reductive elimination of a vicinal trifluoracetoxy sulfone (see 22→23 → 24 and 25). The synthesis of intermediates anticipating potential macrolactonization are also described. © 1990, American Chemical Society. All rights reserved.

引用

页码：2786 / 2797

页数：12

共 39 条

[1] A MECHANISTIC STUDY OF THE FK-506 TRICARBONYL SYSTEM REARRANGEMENT - SYNTHESIS OF C.9 LABELED FK-506
ASKIN, D
REAMER, RA
JOE, D
VOLANTE, RP
SHINKAI, I
[J]. TETRAHEDRON LETTERS, 1989, 30 (45) : 6121 - 6124
[2] CHEMISTRY OF FK-506 - BENZILIC ACID REARRANGEMENT OF THE TRICARBONYL SYSTEM
ASKIN, D
REAMER, RA
JONES, TK
VOLANTE, RP
SHINKAI, I
[J]. TETRAHEDRON LETTERS, 1989, 30 (06) : 671 - 674
[3] PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION
BODEN, EP
KECK, GE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) : 2394 - 2395
[4] Burgess E. M., 1977, ORG SYNTH, V56, P40
[5] THERMAL REACTIONS OF ALKYL N-CARBOMETHOXYSULFAMATE ESTERS
BURGESS, EM
PENTON, HR
TAYLOR, EA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) : 26 - 31
[6] CALNE RY, 1989, LANCET, P227
[7] COLEMAN RS, 1989, HETEROCYCLES, V28, P157
[8] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 4155 - 4156
[9] Evans D. A., 1982, ALDRICHIM ACTA, V15, P23
[10] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES
EVANS, DA
NELSON, JV
VOGEL, E
TABER, TR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) : 3099 - 3111

← 1 2 3 4 →