A simple asymmetric synthesis of cis-2,6-disubstituted tetrahydropyran acetic acid derivatives

被引：34

作者：

Edmunds, AJF

Trueb, W

机构：

[1] Sandoz Agro AG

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(96)02483-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new asymmetric synthesis of functionalised cis-2,6-disubstituted tetrahydropyran acetic acids is described. The utility of the procedure is illustrated by the synthesis of (+) and (-)-(cis-6-methyltetrahydropyran-2-yl)acetic acid, a glandular secretion of the civet cat (Viverra civetta). (C) 1997, Elsevier Science Ltd.

引用

页码：1009 / 1012

页数：4

共 17 条

[1] Michael addition of N- and O-centred nucleophiles to tethered acrylates. The role of double bond geometry in controlling the diastereoselectivity of cyclisations leading to 2,6-disubstituted tetrahydropyrans and piperidines
Banwell, MG
Bui, CT
Pham, HTT
Simpson, GW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (10): : 967 - 969
[2] BANWELL MG, 1996, J CHEM SOC CHEM COMM, P723
[3] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS
BOIVIN, TLB
[J]. TETRAHEDRON, 1987, 43 (15) : 3309 - 3362
[4] IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS
CRISPINO, GA
JEONG, KS
KOLB, HC
WANG, ZM
XU, DQ
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) : 3785 - 3786
[5] ENZYMES IN ORGANIC-SYNTHESIS .36. SYNTHESIS OF OPTICALLY-ACTIVE CIVET CONSTITUENT FROM AN ENZYME-GENERATED CHIRAL SYNTHON
JONES, JB
HINKS, RS
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (04): : 704 - 707
[6] KOCIENSKI P, 1996, SYNTHESIS-STUTTGART, P652
[7] CATALYTIC ASYMMETRIC DIHYDROXYLATION
KOLB, HC
VANNIEUWENHZE, MS
SHARPLESS, KB
[J]. CHEMICAL REVIEWS, 1994, 94 (08) : 2483 - 2547
[8] TOTAL SYNTHESIS OF (+)-DECARESTRICTINE-L
MACHINAGA, N
KIBAYASHI, C
[J]. TETRAHEDRON LETTERS, 1993, 34 (36) : 5739 - 5742
[9] MANCUSO AJ, 1981, SYNTHESIS-STUTTGART, P165
[10] A HIGHLY STEREOSELECTIVE SYNTHETIC METHOD FOR CIS-2-HYDROXYMETHYL-6-ALKYLTETRAHYDROPYRANS
MANDAI, T
UEDA, M
KASHIWAGI, K
KAWADA, M
TSUJI, J
[J]. TETRAHEDRON LETTERS, 1993, 34 (01) : 111 - 114

← 1 2 →