Literature DB >> 15273284

The total synthesis of (-)-crispatene.

Aubry K Miller1, Daniel H Byun, Christopher M Beaudry, Dirk Trauner.   

Abstract

The total synthesis of the molluscan polypropionate (-)-crispatene is described. The synthesis features a palladium-catalyzed cross-coupling to establish a sensitive conjugated tetraene and its Lewis acid-catalyzed cycloisomerization to yield the bicyclo[3.1.0]hexene core of the natural product. The absolute configuration of (-)-crispatene and related molecules is established.

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Year:  2004        PMID: 15273284      PMCID: PMC514427          DOI: 10.1073/pnas.0401787101

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  8 in total

1.  SNF4435C and D, novel immunosuppressants produced by a strain of Streptomyces spectabilis. I. Taxonomy, fermentation, isolation and biological activities.

Authors:  K Kurosawa; K Takahashi; E Tsuda
Journal:  J Antibiot (Tokyo)       Date:  2001-07       Impact factor: 2.649

2.  Synthetic studies toward SNF4435 C and SNF4435 D.

Authors:  Christopher M Beaudry; Dirk Trauner
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

3.  "Endo" and "exo" bicyclo[4.2.0]-octadiene isomers from the electrocyclization of fully substituted tetraene models for SNF 4435C and D. control of stereochemistry by choice of a functionalized substituent.

Authors:  Kathlyn A Parker; Yeon-Hee Lim
Journal:  Org Lett       Date:  2004-01-22       Impact factor: 6.005

4.  Total synthesis of (+/-)-photodeoxytridachione through a Lewis acid catalyzed cyclization.

Authors:  Aubry K Miller; Dirk Trauner
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-03       Impact factor: 15.336

5.  SNF4435C and D, novel immunosuppressants produced by a strain of Streptomyces spectabilis. II. Structure elucidation.

Authors:  K Takahashi; E Tsuda; K Kurosawa
Journal:  J Antibiot (Tokyo)       Date:  2001-07       Impact factor: 2.649

6.  Convenient Synthesis of Cyclopropylalkanol Derivatives Possessing a Difluoromethylenephosphonate Group at the Ring.

Authors:  Tsutomu Yokomatsu; Hiroshi Abe; Takehiro Yamagishi; Kenji Suemune; Shiroshi Shibuya
Journal:  J Org Chem       Date:  1999-10-29       Impact factor: 4.354

7.  Photosynthetic Marine Mollusks: In vivo 14C Incorporation into Metabolites of the Sacoglossan Placobranchus ocellatus.

Authors:  C Ireland; P J Scheuer
Journal:  Science       Date:  1979-08-31       Impact factor: 47.728

8.  Biomimetic studies on polyenes.

Authors:  John E Moses; Jack E Baldwin; Sébastien Brückner; Serena J Eade; Robert M Adlington
Journal:  Org Biomol Chem       Date:  2003-11-07       Impact factor: 3.876

  8 in total

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