Literature DB >> 12323057

Stereocontrolled synthesis of (+)-boronolide.

Barry M Trost1, Vince S C Yeh.   

Abstract

Boronolide was synthesized stereoselectively from hydroxyacetylfuran 5 and valeraldehyde 6 using a novel dizinc aldol catalyst. Ring closing metathesis provides the lactone ring. The synthesis requires 12 steps and proceeds in 26% overall yield. [reaction: see text]

Entities:  

Mesh:

Substances:

Year:  2002        PMID: 12323057     DOI: 10.1021/ol026665i

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Direct asymmetric Zn-aldol reaction of methyl vinyl ketone and its synthetic applications.

Authors:  Barry M Trost; Seunghoon Shin; Joseph A Sclafani
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

2.  A unified synthetic strategy to the Cryptocarya family of natural products exploiting Anion Relay Chemistry (ARC).

Authors:  Bruno Melillo; Amos B Smith
Journal:  Org Lett       Date:  2013-04-24       Impact factor: 6.005

3.  Synthesis of gem-difluoromethylenated analogues of boronolide.

Authors:  Jing Lin; Xiao-Long Qiu; Feng-Ling Qing
Journal:  Beilstein J Org Chem       Date:  2010-04-20       Impact factor: 2.883

4.  ProPhenol-catalyzed asymmetric additions by spontaneously assembled dinuclear main group metal complexes.

Authors:  Barry M Trost; Mark J Bartlett
Journal:  Acc Chem Res       Date:  2015-02-04       Impact factor: 22.384

Review 5.  Mukaiyama Aldol Reactions in Aqueous Media.

Authors:  Taku Kitanosono; Shū Kobayashi
Journal:  Adv Synth Catal       Date:  2013-10-31       Impact factor: 5.837

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.