Enantiodivergent synthesis of both antipodes of hydroxy-exo-brevicomin from L-(+)-tartaric acid

被引：19

作者：

Prasad, Kavirayani R. ^{[1
]}

Anbarasan, Pazhamalai ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

TETRAHEDRON | 2006年 / 62卷 / 35期

关键词：

stereoselective reduction; L-(+)-tartaric acid; hydroxy-exo-brevicomin; 6,8-dioxabicyclo[3.2.1]octane;

D O I：

10.1016/j.tet.2006.06.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantiodivergent approach to both antipodes of hydroxy-exo-brevicomin was achieved from a common chiral precursor L-(+)-tartaric acid. The strategy utilizes the elaboration of a keto-Weinreb amide and successive stereoselective reductions. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8303 / 8308

页数：6

共 50 条

[41] γ-Hydroxy Amides from Tartaric Acid: Versatile Chiral Building Blocks for the Total Synthesis of Natural Products
Nanda, Laxmi Narayan
Shruthi, Kodambahalli S.
Prasad, Kavirayani R.
CHEMICAL RECORD, 2021, 21 (08): : 1957 - 1967
[42] Practical synthesis of (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its acetate from L-tartaric acid
Tomori, H
Maruyama, H
Ogura, K
HETEROCYCLES, 1996, 43 (02) : 415 - 423
[43] Synthesis of macrocyclic polyhydroxy tetralactams derived from L-tartaric acid and QQ -hydroxyglutaric acid
Arnaud, N.
Picard, C.
Cazaux, L.
Tisnes, P.
Tetrahedron, 53 (40):
[44] CATALYZES BY METAL-COMPLEXES .46. SYNTHESIS OF AN OPTICALLY-ACTIVE SILYLATED DIPHOSPHINE AND RELATED DINITRILE DERIVED FROM L-(+)-TARTARIC ACID
CERNY, M
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1977, 42 (10) : 3069 - 3078
[45] A CONVENIENT SYNTHESIS OF L-(S)-GLYCERALDEHYDE ACETONIDE FROM L-ASCORBIC-ACID
HUBSCHWERLEN, C
SYNTHESIS-STUTTGART, 1986, (11): : 962 - 964
[46] Enantioselective recognition for carboxylic acids by novel chiral macrocyclic polyamides derived from L-/D-tartaric acid
Li, Baohua
Yang, Xuemei
Wu, Xiaojun
Luo, Zengwei
Zhong, Cheng
Fu, Enqin
SUPRAMOLECULAR CHEMISTRY, 2006, 18 (06) : 507 - 513
[47] TARTARIC ACID SYNTHESIS FROM L-ASCORBIC ACID-1-14C IN GRAPE BERRIES
SAITO, K
KASAI, Z
PHYTOCHEMISTRY, 1969, 8 (11) : 2177 - &
[48] ENANTIOSELECTIVE SYNTHESIS OF (+)-(S)-BETA-ANGELICA LACTONE FROM L-TARTARIC ACID
ORTUNO, RM
ALONSO, D
FONT, J
TETRAHEDRON LETTERS, 1986, 27 (09) : 1079 - 1080
[49] Synthesis of macrocyclic polyhydroxy tetralactams derived from L-tartaric acid and beta-hydroxyglutaric acid
Arnaud, N
Picard, C
Cazaux, L
Tisnes, P
TETRAHEDRON, 1997, 53 (40) : 13757 - 13768
[50] Total synthesis of L-biopterin from L-tartaric acid via 5-deoxy-L-arabinose
Fernandez, AM
Duhamel, L
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24): : 8698 - 8700

← 1 2 3 4 5 →