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
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
收藏
页码:547 / 553
页数:7
相关论文
共 32 条
[1]   Natural products - antifungal agents derived from plants [J].
Arif, Tasleem ;
Bhosale, J. D. ;
Kumar, Naresh ;
Mandal, T. K. ;
Bendre, R. S. ;
Lavekar, G. S. ;
Dabur, Rajesh .
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2009, 11 (07) :621-638
[2]   FUNGAL MACROLIDES - STRUCTURE DETERMINATION AND BIOSYNTHESIS OF ACHAETOLIDE, A LACTONE FROM ACHAETOMIUM-CRISTALLIFERUM [J].
BODO, B ;
MOLHO, L ;
DAVOUST, D ;
MOLHO, D .
PHYTOCHEMISTRY, 1983, 22 (02) :447-451
[3]   First total synthesis of achaetolide [J].
Chandrasekhar, S. ;
Balaji, S. V. ;
Rajesh, G. .
TETRAHEDRON LETTERS, 2010, 51 (39) :5164-5166
[4]   Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones [J].
Crimmins, MT ;
King, BW ;
Tabet, EA ;
Chaudhary, K .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :894-902
[5]   Titanium enolates of thiazolidinethione chiral auxiliaries: Versatile tools for asymmetric aldol additions [J].
Crimmins, MT ;
Chaudhary, K .
ORGANIC LETTERS, 2000, 2 (06) :775-777
[6]  
Croteau R., 2000, Biochemistry & molecular biology of plants, V24, P1250, DOI DOI 10.1201/B11003-3
[7]   First asymmetric synthesis of achaetolide [J].
Das, Tapas ;
Bhuniya, Rajib ;
Nanda, Samik .
TETRAHEDRON-ASYMMETRY, 2010, 21 (18) :2206-2211
[8]   Decanolides, 10-membered lactones of natural origin [J].
Drager, G ;
Kirschning, A ;
Thiericke, R ;
Zerlin, M .
NATURAL PRODUCT REPORTS, 1996, 13 (05) :365-375
[9]   Stagonolides G-I and Modiolide A, Nonenolides Produced by Stagonospora cirsii, a Potential Mycoherbicide for Cirsium arvense [J].
Evidente, Antonio ;
Cimmino, Alessio ;
Berestetskiy, Alexander ;
Andolfi, Anna ;
Motta, Andrea .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (11) :1897-1901
[10]   Stagonolides B-F, nonenolides produced by Stagonospora cirsii, a potential mycoherbicide of Cirsium arvense [J].
Evidente, Antonio ;
Cimmino, Alessio ;
Berestetskiy, Alexander ;
Mitina, Galina ;
Andolfi, Anna ;
Motta, Andrea .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (01) :31-34