THE CYCLIZATION ROUTE TO THE CALCITRIOL A-RING - A FORMAL SYNTHESIS OF (+)-1-ALPHA,25-DIHYDROXYVITAMIN-D(3)

被引：25

作者：

CHEN, C ^{[1
]}

CRICH, D ^{[1
]}

机构：

[1] UNIV ILLINOIS,DEPT CHEM,M-C 111,801 W TAYLOR ST,CHICAGO,IL 60607

来源：

TETRAHEDRON | 1993年 / 49卷 / 36期

关键词：

D O I：

10.1016/S0040-4020(01)88018-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient asymmetric synthesis of the A-ring of 1alpha,25-dihydroxyvitamin D3 from alpha-bromoacrolein is described. The key steps of the synthesis are the Evans type syn-selective asymmetric aldol reaction of bromoacrolein with the boron enolate of 3-chloroacetyl-4(S)-isopropyl oxazolidinone and ring closure by Heck type reaction of a vinyl bromide onto an alpha,beta-unsaturated ester in the exo-mode.

引用

页码：7943 / 7954

页数：12

共 60 条

[1] ALDOL CONDENSATIONS OF CHIRAL ALPHA-HALOIMIDATES - A CHIRAL DARZENS CONDENSATION PROCEDURE
ABDELMAGID, A
LANTOS, I
PRIDGEN, LN
[J]. TETRAHEDRON LETTERS, 1984, 25 (31) : 3273 - 3276
[2] METAL-ASSISTED ALDOL CONDENSATION OF CHIRAL ALPHA-HALOGENATED IMIDE ENOLATES - A STEREOCONTROLLED CHIRAL EPOXIDE SYNTHESIS
ABDELMAGID, A
PRIDGEN, LN
EGGLESTON, DS
LANTOS, I
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) : 4595 - 4602
[3] 5-BROMO-2-PYRONE - AN EASILY PREPARED AMBIPHILIC DIENE AND A SYNTHETIC EQUIVALENT OF 2-PYRONE IN MILD, THERMAL, DIELS-ALDER CYCLOADDITIONS
AFARINKIA, K
POSNER, GH
[J]. TETRAHEDRON LETTERS, 1992, 33 (51) : 7839 - 7842
[4] STEREOSELECTIVE TOTAL SYNTHESIS OF "1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL
BAGGIOLINI, EG
IACOBELLI, JA
HENNESSY, BM
USKOKOVIC, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (10) : 2945 - 2948
[5] STEREOCONTROLLED TOTAL SYNTHESIS OF "1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL AND 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL
BAGGIOLINI, EG
IACOBELLI, JA
HENNESSY, BM
BATCHO, AD
SERENO, JF
USKOKOVIC, MR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) : 3098 - 3108
[6] DEHYDROGENATION OF STEROIDAL AND TRITERPENOID KETONES USING BENZENESELENINIC ANHYDRIDE
BARTON, DHR
LESTER, DJ
LEY, SV
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (10): : 2209 - 2212
[7] ACYL RADICAL CYCLIZATIONS IN SYNTHESIS .3. SYNTHESIS OF (+/-)-TRANS-3,5-BIS-(TERT-BUTYLDIMETHYLSILOXY)-2-METHYLENECYCLOHEXANONE, AN A-RING MODEL FOR 1-ALPHA, 25-DIHYDROXYVITAMIN-D3
BATTY, D
CRICH, D
FORTT, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11): : 2875 - 2879
[8] BATTY D, 1992, J CHEM SOC P1, P2894
[9] BATTY D, 1992, THESIS U LONDON
[10] SYNTHESIS OF TRIPEPTIDE-S AND TETRAPEPTIDE-S - THE EXTENDED C-TERMINUS OF BLEOMYCIN-A2
BOGER, DL
MENEZES, RF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (16) : 4331 - 4333

← 1 2 3 4 5 6 →