The stereoselective total synthesis of (-)-achaetolide

被引：11

作者：

Thakur, Pallavi ^{[1
]}

Kumaraswamy, Boyapelly ^{[1
]}

Reddy, Gurram Raji ^{[1
]}

Bandichhor, Rakeshwar ^{[2
]}

Mukkantii, Khagga ^{[3
]}

机构：

[1] Maithili Life Sci Pvt Ltd, IDA, Hyderabad 500076, Andhra Pradesh, India

[2] Dr Reddys Labs Ltd, IPD, Qutubullapur 500073, Andhra Pradesh, India

[3] JNT Univ, Ctr Environm Sci, Inst Sci & Technol, Hyderabad 500072, Andhra Pradesh, India

来源：

TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 08期

关键词：

POTENTIAL MYCOHERBICIDE; PHYTOTOXIC NONENOLIDE; STAGONOSPORA-CIRSII; ALDOL ADDITIONS; ACHAETOLIDE; LACTONE; AUXILIARIES; MACROLIDES; MODIOLIDE;

D O I：

10.1016/j.tetasy.2012.03.010

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The stereoselective total synthesis of (-)-achaetolide is described in a convergent manner. Grignard addition, Wittig homologation, acetate aldol and ring closing metathesis reactions were the key steps involved. The required olefinic alcohol fragments were synthesized from a single chiral pool material 2-deoxy-D-ribose and olefinic acid fragment was prepared from acetate aldol reaction. Both the olefinic acid and alcohols were prepared in a concise method. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：547 / 553

页数：7

共 50 条

[1] Stereoselective total synthesis of achaetolide and reconfirmation of its absolute configuration
Srihari, P.
Kumaraswamy, B.
Shankar, P.
Ravishashidhar, V.
Yadav, J. S.
TETRAHEDRON LETTERS, 2010, 51 (47) : 6174 - 6176
[2] Stereoselective Total Synthesis of Achaetolide from L-Malic Acid
Sabitha, Gowravaram
Srinivas, Rangavajjula
Yadav, Jhillu S.
SYNTHESIS-STUTTGART, 2011, (20): : 3343 - 3349
[3] First total synthesis of achaetolide
Chandrasekhar, S.
Balaji, S. V.
Rajesh, G.
TETRAHEDRON LETTERS, 2010, 51 (39) : 5164 - 5166
[4] Total Synthesis of Achaetolide from D-Mannitol
Rao, K. Sripad
Chattapadhyay, Amit Kumar
Ghosh, Subhash
SYNLETT, 2010, (20) : 3078 - 3080
[5] First asymmetric synthesis of achaetolide
Das, Tapas
Bhuniya, Rajib
Nanda, Samik
TETRAHEDRON-ASYMMETRY, 2010, 21 (18) : 2206 - 2211
[6] Stereoselective total synthesis of (-)-borrelidin
Vong, BG
Kim, SH
Abraham, S
Theodorakis, EA
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) : 3947 - 3951
[7] Stereoselective total synthesis of (+)-norrisolide
Brady, TP
Kim, SH
Wen, K
Theodorakis, EA
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (06) : 739 - 742
[8] Stereoselective Total Synthesis of Carolacton
Kuilya, Tapan Kumar
Goswami, Rajib Kumar
ORGANIC LETTERS, 2017, 19 (09) : 2366 - 2369
[9] A STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-OXYLUBIMIN
IWATA, C
TAKEMOTO, Y
KUBOTA, H
KURODA, T
IMANISHI, T
TETRAHEDRON LETTERS, 1985, 26 (27) : 3231 - 3234
[10] Stereoselective total synthesis of chrysanthemol
Mou, LY
Zhu, LY
Liang, XT
CHINESE CHEMICAL LETTERS, 1998, 9 (10) : 929 - 930

← 1 2 3 4 5 →