Stereoselective synthesis of C1-C9 and C9-C17 fragments of (+)-13-deoxytedanolide

被引：7

作者：

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

Reddy, N. Rami ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500607, Andhra Pradesh, India

来源：

TETRAHEDRON | 2010年 / 66卷 / 17期

关键词：

(+)-13-Deoxytedanolide; Cytotoxicity; Evans' aldol; Chiral auxiliary; Cross-metathesis; Yamaguchi macrolactonization; Regioselective Sharpless asymmetric dihydroxylation; 18-MEMBERED ANTITUMOR MACROLIDE; EFFICIENT SHARPLESS DIHYDROXYLATION; ASYMMETRIC DIHYDROXYLATION; ALDOL CONDENSATIONS; DIVERGENT APPROACH; PROTECTING GROUP; C-13-C23; PART; SECO-ACID; TEDANOLIDE; MYRIAPORONES;

D O I：

10.1016/j.tet.2010.01.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and highly stereoselective asymmetric synthesis of C1-C9 and C9-C17 fragments of (+)-13-deoxytedanolide have been achieved. Utilization of desymmetrization technique to prepare the triol with five stereogenic centers, regioselective Sharpless asymmetric dillydroxylation, Evans' aldol reaction, chiral methylation, and Wittig olefination are highlights of the synthesis. (C) 2010 Published by Elsevier Ltd.

引用

页码：3265 / 3274

页数：10

共 50 条

[41] A synthetic approach towards the C1-C9 subunit of zincophorin
Cossy, J
Blanchard, N
Defosseux, M
Meyer, C
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (12) : 2144 - 2146
[42] Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C
Bates, Robert H.
Shotwell, J. Brad
Roush, William R.
ORGANIC LETTERS, 2008, 10 (19) : 4343 - 4346
[43] Synthesis of C1-C8 and C9-C24 fragments of (-)-discodermolide: use of asymmetric alkylation and stereoselective aldol reactions
Filla, SA
Song, JJ
Chen, LR
Masamune, S
TETRAHEDRON LETTERS, 1999, 40 (30) : 5449 - 5453
[44] Formal Synthesis of the Bryostatin Northern Hemisphere: Asymmetric Synthesis of the B Ring and C1-C9 Fragment
Nakagawa-Goto, Kyoko
Crimmins, Michael T.
SYNLETT, 2011, (10) : 1413 - 1418
[45] SYNTHETIC STUDIES RELATING TO THE C1-C9 EASTERN HALF OF ROSARAMICIN
SUNAY, U
FRASERREID, B
TETRAHEDRON LETTERS, 1986, 27 (44) : 5335 - 5338
[46] Stereoselective synthesis of C3-C10 and C13-C21 fragments of laulimalide
Punna, Sreenivas
Rakesh
Prabhakar, Anabathula
Sharma, Gangavaram V. M.
Kunwar, Ajit Chand
LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (06) : 447 - 454
[47] SYNTHESIS OF MACROCYCLIC ANTIBIOTICS .9. SYNTHESIS OF THE C-9-C-13 FRAGMENTS OF 12-EPINEOMETHINOLIDE AND METHINOLIDE
SVIRIDOV, AF
YASHUNSKII, DV
ERMOLENKO, MS
BORODKIN, VS
KOCHETKOV, NK
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1986, 35 (11): : 2351 - 2355
[48] STEREOCONTROLLED OSMYLATION OF MEDIUM-RING ALKENES - SYNTHESIS OF A C1-C9 ERYTHRONOLIDE FRAGMENT
VEDEJS, E
DOLPHIN, JM
MASTALERZ, H
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (01) : 127 - 130
[49] Synthesis of the C1-C9 core of bengazole A: Harnessing the ambident nucleophilicity of 2-lithiooxazole
Shafer, CM
Molinski, TF
TETRAHEDRON LETTERS, 1998, 39 (19) : 2903 - 2906
[50] A Highly Stereoselective, Efficient, and Scalable Synthesis of the C(1)-C(9) Fragment of the Epothilones
Foley, Corinne N.
Leighton, James L.
ORGANIC LETTERS, 2015, 17 (23) : 5858 - 5861

← 1 2 3 4 5 →