A novel strategy for the chiral 2,4,5-triol moiety and its application to the synthesis of seimatopolide A and (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide

被引：22

作者：

Reddy, B. Phaneendra ^{[1
]}

Pandurangam, T. ^{[1
]}

Yadav, J. S. ^{[1
]}

Reddy, B. V. Subba ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 43期

关键词：

Prins cyclization; McMillan aminoxylation; 2,4,5-Triols; Ring closing metathesis; STEREOSELECTIVE TOTAL-SYNTHESIS; RING-CLOSING METATHESIS; PRINS CYCLIZATION; CHOLESTEROL-BIOSYNTHESIS; SECONDARY METABOLITES; DECARESTRICTINES; PENICILLIUM; INHIBITORS; MACROLIDES; LACTONES;

D O I：

10.1016/j.tetlet.2012.08.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective approach to the total synthesis of seimatopolide A and (25,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide is described via a common polyketide precursor by means of Prins reaction and MacMillan aminoxylation sequence. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5749 / 5752

页数：4

共 31 条

[1] NOVEL CONVERSION OF EPOXIDES TO ONE-CARBON HOMOLOGATED ALLYLIC ALCOHOLS BY DIMETHYLSULFONIUM METHYLIDE
ALCARAZ, L
HARNETT, JJ
MIOSKOWSKI, C
MARTEL, JP
LEGALL, T
SHIN, DS
FALCK, JR
[J]. TETRAHEDRON LETTERS, 1994, 35 (30) : 5449 - 5452
[2] CHEMICAL INVESTIGATION OF THE METABOLITES FROM THE CANADIAN TUCKAHOE, POLYPORUS-TUBERASTER
AYER, WA
SUN, M
BROWNE, LM
BRINEN, LS
CLARDY, J
[J]. JOURNAL OF NATURAL PRODUCTS, 1992, 55 (05): : 649 - 653
[3] Saturated and unsaturated lactones
Collins, I
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (11): : 1377 - 1395
[4] ASCIDIATRIENOLIDE-A IS A 10-MEMBERED LACTONE
CONGREVE, MS
HOLMES, AB
HUGHES, AB
LOONEY, MG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) : 5815 - 5816
[5] Enantioselective total synthesis of (+)-gigantecin: Exploiting the asymmetric glycolate aldol reaction
Crimmins, MT
She, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (40) : 12790 - 12791
[6] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis
Deiters, A
Martin, SF
[J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2199 - 2238
[7] Decanolides, 10-membered lactones of natural origin
Drager, G
Kirschning, A
Thiericke, R
Zerlin, M
[J]. NATURAL PRODUCT REPORTS, 1996, 13 (05) : 365 - 375
[8] GOHRT A, 1992, J ANTIBIOT, V45, P66
[9] SECONDARY METABOLITES BY CHEMICAL-SCREENING .8. DECARESTRICTINES, A NEW FAMILY OF INHIBITORS OF CHOLESTEROL-BIOSYNTHESIS FROM PENICILLIUM .1. STRAIN DESCRIPTION, FERMENTATION, ISOLATION AND PROPERTIES
GRABLEY, S
GRANZER, E
HUTTER, K
LUDWIG, D
MAYER, M
THIERICKE, R
TILL, G
WINK, J
PHILIPS, S
ZEECK, A
[J]. JOURNAL OF ANTIBIOTICS, 1992, 45 (01) : 56 - 65
[10] RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS
GRUBBS, RH
MILLER, SJ
FU, GC
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) : 446 - 452

← 1 2 3 4 →