Literature DB >> 17447815

Enantioselective synthesis of (+)-majusculone.

Douglass F Taber1, M Inthikhab Sikkander, Pierre H Storck.   

Abstract

The first enantioselective synthesis of a chamigrane sesquiterpene, (+)-majusculone, has been completed. The quaternary center was generated asymmetrically by alkylidene carbene insertion, with retention of absolute configuration, from a diastereomerically pure ketal.

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Year:  2007        PMID： 17447815      PMCID： PMC3248824          DOI： 10.1021/jo070257g

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

1.  Enantioselective ring construction: synthesis of halogenated marine natural spiro[5.5]undecane sesquiterpenes.

Authors:  J D Martin; C Perez; J L Ravelo
Journal:  J Am Chem Soc       Date:  1986-11-01       Impact factor: 15.419

2.  Application of chiral lanthanide shift reagents for assignment of absolute configuration of alcohols.

Authors:  Indranath Ghosh; Hongbo Zeng; Yoshito Kishi
Journal:  Org Lett       Date:  2004-12-09       Impact factor: 6.005

3.  A formal synthesis of (+)-lactacystin.

Authors:  Duncan J Wardrop; Edward G Bowen
Journal:  Chem Commun (Camb)       Date:  2005-09-19       Impact factor: 6.222

4.  New sesquiterpene derivatives from the red alga Laurencia scoparia. Isolation, structure determination, and anthelmintic activity.

Authors:  D Davyt; R Fernandez; L Suescun; A W Mombrú; J Saldaña; L Domínguez; J Coll; M T Fujii; E Manta
Journal:  J Nat Prod       Date:  2001-12       Impact factor: 4.050

5.  Studies on the biosynthesis of cholesterol. XX. Steric course of decarboxylation of 5-pyrophosphomevalonate and of the carbon to carbon bond formation in the biosynthesis of farnesyl pyrophosphate.

Authors:  J W Cornforth; R H Cornforth; G Popják; L Yengoyan
Journal:  J Biol Chem       Date:  1966-09-10       Impact factor: 5.157

6.  Synthesis of (-)-morphine.

Authors:  Douglass F Taber; Timothy D Neubert; Arnold L Rheingold
Journal:  J Am Chem Soc       Date:  2002-10-23       Impact factor: 15.419

7.  Novel rearrangements of sesquiterpenoid panasinsane derivatives under acidic conditions.

Authors:  C F Amigo; I G Collado; J R Hanson; R Hernández-Galán; P B Hitchcock; A J Macías-Sánchez; D J Mobbs
Journal:  J Org Chem       Date:  2001-06-15       Impact factor: 4.354

8.  Enantioselective construction of cyclic quaternary centers: (-)-mesembrine.

Authors:  D F Taber; T D Neubert
Journal:  J Org Chem       Date:  2001-01-12       Impact factor: 4.354
  8 in total
  4 in total

1.  The catalytic asymmetric total synthesis of elatol.

Authors:  David E White; Ian C Stewart; Robert H Grubbs; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2007-12-29       Impact factor: 15.419

2.  Transition-metal-free chemo- and regioselective vinylation of azaallyls.

Authors:  Minyan Li; Osvaldo Gutierrez; Simon Berritt; Ana Pascual-Escudero; Ahmet Yeşilçimen; Xiaodong Yang; Javier Adrio; Georgia Huang; Eiko Nakamaru-Ogiso; Marisa C Kozlowski; Patrick J Walsh
Journal:  Nat Chem       Date:  2017-04-17       Impact factor: 24.427

3.  A general enantioselective route to the chamigrene natural product family.

Authors:  David E White; Ian C Stewart; Brinton A Seashore-Ludlow; Robert H Grubbs; Brian M Stoltz
Journal:  Tetrahedron       Date:  2010-03-26       Impact factor: 2.457

4.  Preparation of chiral 3-oxocycloalkanecarbonitrile and its derivatives by crystallization-induced diastereomer transformation of ketals with chiral 1,2-diphenylethane-1,2-diol.

Authors:  Yohei Yamashita; Daisuke Maki; Shiho Sakurai; Takumi Fuse; Shoji Matsumoto; Motohiro Akazome
Journal:  RSC Adv       Date:  2018-09-21       Impact factor: 3.361
  4 in total

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