Stereo selective total synthesis of (3R) , (5R)-5-hydroxy-de-O-methyllasiodiplodin

被引：0

作者：

Narendra, Saikam ^{[1
,2
]}

Sanasi, Paul Douglas ^{[1
]}

Leleti, Krishnakanth Reddy ^{[2
,3
]}

Murahari, Kiran Kumar ^{[2
]}

机构：

[1] Andhra Univ, Dept Engn Chem, Coll Engn A, Visakhapatnam 530003, AP, India

[2] Aragen Life Sci Pvt Ltd, GVK Biosci Pvt Ltd, Chem Serv, IDA, Hyderabad 500076, Telangana, India

[3] Sai Life Sci Ltd, Med Chem Div, ICICI knowledge Pk, Hyderabad 500078, Telangana, India

来源：

CHEMICAL DATA COLLECTIONS | 2024年 / 54卷

关键词：

Lasiodiplodins; (5R)-5-hydroxy-de-O-methyllasiodiplodin; Grignard reaction; Yamaguchi macrolactonization; (3R); OLEFIN-METATHESIS CATALYSTS; PROTECTING GROUP; METABOLITES; MACROCYCLES; RHIZOSPHERE; CURVULARIN; COMPOUND; STRAIN; RCM;

D O I：

10.1016/j.cdc.2024.101169

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient stereoselective total synthesis of ( 3 R ),(5 R )-5 - hydroxy-de- O-methyllasiodiplodin has been accomplished starting from commercially available materials. The key steps involved in this synthesis are Grignard reaction, Yamaguchi esterification and RCM reaction.

引用

页数：7

共 40 条

[1] METABOLITES OF LASIODIPLODIA-THEOBROMAE [J].

ALDRIDGE, DC ;

GALT, S ;

GILES, D ;

TURNER, WB .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (09) :1623-&

[2] Olefin metathesis: The early days (Nobel lecture) [J].

Chauvin, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) :3740-3747

[3] The exploration of macrocycles for drug discovery - an underexploited structural class [J].

Driggers, Edward M. ;

Hale, Stephen P. ;

Lee, Jinbo ;

Terrett, Nicholas K. .

NATURE REVIEWS DRUG DISCOVERY, 2008, 7 (07) :608-624

[4] Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua [J].

Edrada, RA ;

Heubes, M ;

Brauers, G ;

Wray, V ;

Berg, A ;

Gräfe, U ;

Wohlfarth, M ;

Mühlbacher, J ;

Schaumann, K ;

Sudarsono ;

Bringmann, G ;

Proksch, P .

JOURNAL OF NATURAL PRODUCTS, 2002, 65 (11) :1598-1604

[5] SELECTIVE ALLYLATION OF CARBONYL-COMPOUNDS IN AQUEOUS-MEDIA [J].

EINHORN, C ;

LUCHE, JL .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 322 (02) :177-183

[6] Total synthesis of aspercyclide C [J].

Fürstner, A ;

Müller, C .

CHEMICAL COMMUNICATIONS, 2005, (44) :5583-5585

[7] 2-(TRIMETHYLSILYL)ETHYL ESTERS AS CARBOXYL PROTECTING GROUP - APPLICATION IN SYNTHESIS OF (-)-(S)-CURVULARIN [J].

GERLACH, H .

HELVETICA CHIMICA ACTA, 1977, 60 (08) :3039-3044

[8] 6-CHLORODEHYDROCURVULARIN, A NEW METABOLITE FROM COCHLIOBOLUS SPICIFER [J].

GHISALBERTI, EL ;

ROWLAND, CY .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (12) :2175-2177

[9] Effect of the allylic substituents on ring closing metathesis: the total synthesis of stagonolide B and 4-epi-stagonolide B [J].

Giri, Awadut G. ;

Mondal, Mohabul A. ;

Puranik, Vedavati G. ;

Ramana, Chepuri V. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (02) :398-406

[10] Olefin-metathesis catalysts for the preparation of molecules and materials (Nobel lecture) [J].

Grubbs, Robert H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) :3760-3765

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