THE STEREOCHEMICALLY CONTROLLED SYNTHESIS OF SPIROCYCLIC ETHERS AND LACTONES WITH MEDIUM-SIZED (7-MEMBERED, 8-MEMBERED, AND 12-MEMBERED) CARBOCYCLIC RINGS BY PHENYLTHIO MIGRATION - 1-OXASPIRO[4.N]ALKANES AND ALKAN-2-ONES WITH N = 6, 7, AND 11

被引：4

作者：

CHIBALE, K

HARTLEY, RC

JENKINS, KP

SIMONS, M

WARREN, S

RICHARDS, IC

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND

[2] SCHERING AGROCHEM LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLAND

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(00)61701-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Methyl-4-phenylthio-1-oxaspiro[4.6]undecanes, [4.7]dodecanes, [4.11]hexadecanes and the corresponding 2-ones (lactones) can be made from cyclohepta-, octa-, and dodecanone by chain extension to the 2-phenylthio-carbaldehyde, stereoselective aldol reaction and stereospecific phenylthio migration with control over the relative (3,4-syn or anti) and absolute (R or S at positions 3 and 4) stereochemistry.

引用

页码：6783 / 6786

页数：4

共 20 条

[1] TRANSFORMATION OF CYCLIC ALPHA-PHENYLTHIO ALDEHYDES BY STEREOSELECTIVE ALDOL REACTIONS AND PHENYLTHIO MIGRATION INTO SPIROCYCLIC LACTONES AND ETHERS, AND E-ALLYLIC ALCOHOLS WITH 1,4-RELATED CHIRAL CENTERS
AGGARWAL, VK
COLDHAM, I
MCINTYRE, S
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02): : 451 - 460
[2] 3,3-DIETHOXYPROPYL-LITHIUM - A MASKED LITHIUM PROPANAL HOMOENOLATE IN ORGANIC-SYNTHESIS
BARLUENGA, J
FERNANDEZ, JR
RUBIERA, C
YUS, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12): : 3113 - 3117
[3] GAMMA-HYDROXYACETYLENIC ACID-DERIVATIVES - GENERATION FROM PROPIOLIC ACID AND ESTER ANIONS AND THEIR USE IN BUTENOLIDE SYNTHESIS
CARLSON, RM
PETERSON, JR
HOOP, BJ
JENSEN, KJ
[J]. SYNTHETIC COMMUNICATIONS, 1982, 12 (12) : 977 - 982
[4] ASYMMETRIC-SYNTHESIS OF SPIROCYCLIC PYRROLIDINES AND TETRAHYDROFURANS BY CHIRAL ALDOL REACTIONS AND PHENYLTHIO MIGRATION
CHIBALE, K
WARREN, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (45) : 6645 - 6648
[5] STEREOSPECIFIC PHENYLTHIO MIGRATIONS IN THE SYNTHESIS OF SPIROCYCLIC LACTONES AND ETHERS FROM N-METHYL-4-PIPERIDONE AND QUINUCLIDIN-3-ONE
COLDHAM, I
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (18): : 2303 - 2307
[6] CZUK R, 1991, TETRAHEDRON, V47, P7037
[7] DEGROOT A, 1985, SYNTHESIS-STUTTGART, P434
[8] A NOVEL SYNTHESIS OF ALPHA-SULFENYLATED ALDEHYDES
DEGROOT, A
JANSEN, BJM
[J]. TETRAHEDRON LETTERS, 1981, 22 (09) : 887 - 888
[9] El Ali B, 1991, J ORG CHEM, V56, P5357
[10] SAMARIUM(II) DI-IODIDE INDUCED REDUCTIVE COUPLING OF ALPHA,BETA-UNSATURATED ESTERS WITH CARBONYL-COMPOUNDS LEADING TO A FACILE SYNTHESIS OF GAMMA-LACTONE
FUKUZAWA, S
NAKANISHI, A
FUJINAMI, T
SAKAI, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07): : 1669 - 1675

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