Stereoselective synthesis of (3R,6S)-6-hydroxylasiodiplodin

被引：3

作者：

Bujaranipalli, Sheshurao ^{[1
]}

Das, Saibal ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 15期

关键词：

Lasiodiplodin; Natural products; Keck asymmetric allylation; Stille coupling; De Brabander's esterification; Ring closing metathesis; RESORCYLIC ACID LACTONES; LASIODIPLODIA-THEOBROMAE; ENDOPHYTIC FUNGUS; NMR; BIOSYNTHESIS; METABOLITES; DERIVATIVES; INHIBITION; FACILE; CHAIN;

D O I：

10.1016/j.tetlet.2016.02.096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first stereoselective synthesis of polyketide natural product (3R,6S)-6-hydroxylasiodiplodin (1) has been described starting from commonly available starting materials D-mannitol and 2,4,6-trihydroxybenzoic acid. The key reactions involved are Keck asymmetric allylation, Stille coupling, De Brabander's esterification, and ring-closing metathesis (RCM) reaction. The total synthesis was achieved in 19.3% overall yield making the route significant. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：1653 / 1655

页数：3

共 50 条

[21] SYNTHESIS OF OPTICALLY-ACTIVE METHYL (-)-(2R,3R,6S,8S)-NONACTATE
GOMBOS, J
HASLINGER, E
ZAK, H
SCHMIDT, U
MONATSHEFTE FUR CHEMIE, 1975, 106 (01): : 219 - 222
[22] Synthesis of (3R,6R)- and (3S,6R)-piperidinone PNA
Püschl, A
Boesen, T
Tedeschi, T
Dahl, O
Nielsen, PE
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (21): : 2757 - 2763
[23] A Short and Stereoselective Synthesis of the (-)-(5R,6S)-6-Acetoxy-hexadecane-5-olide
Bin SUN1
Chinese Chemical Letters, 2004, (10) : 1177 - 1178
[24] STEREOSELECTIVE SYNTHESIS OF A (5R,6S)-6-[(R)-1-HYDROXYETHYL]-2-ARYLOXYPENEM
COOKE, MD
MOORE, KW
ROSS, BC
TURNER, SE
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (18) : 1005 - 1006
[25] A facile synthesis of (6S,1′S)-(+)-hernandulcin and (6S,1′R)-(+)-epihernandulcin
Kim, JH
Lim, HJ
Cheon, SH
TETRAHEDRON, 2003, 59 (38) : 7501 - 7507
[26] An efficient conversion of (3R,3′R,6′R)-lutein to (3R,3′S,6′R)-lutein (3′-epilutein) and (3R,3′R)-zeaxanthin
Khachik, F
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (01): : 67 - 72
[27] ENANTIO AND STEREOSELECTIVE SYNTHESIS OF (5R,6S)-6-ACETOXYHEXADECANOLIDE, A MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE
BONINI, C
CHECCONI, M
RIGHI, G
ROSSI, L
TETRAHEDRON, 1995, 51 (14) : 4111 - 4116
[28] A SYNTHESIS OF ENANTIOMERICALLY PURE (3S,6R)-3,6-DIMETHYLTETRAHYDROPYRAN-2-ONE AND (3R,6S)-3,6-DIMETHYLTETRAHYDROPYRAN-2-ONE
BERNARDI, R
GHIRINGHELLI, D
SYNTHESIS-STUTTGART, 1989, (12): : 938 - 939
[29] (1S,3R,6S,7R)-3,7-Dichloro-trans-himachalane
Ourhriss, Najia
Mazoir, Noureddine
Daran, Jean-Claude
Berraho, Moha
Benharref, Ahmed
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : o1497 - o1499
[30] Synthesis and herbicidal activity of [3R*,5S*,6S*]-3-benzyloxy-5-methoxy-1,7-dioxaspiro[5.5]undecane and [3R*,5S*,6S*]-3-methoxy-5-benzyloxy-1,7-dioxaspiro[5.5]undecane
Brimble, MA
Johnston, AD
Furneaux, RH
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03): : 471 - 479

← 1 2 3 4 5 →