Literature DB >> 10768196

Synthesis of the C16-C28 spiroketal subunit of spongistatin 1 (altohyrtin A): the pyrone approach.

M T Crimmins1, J D Katz.   

Abstract

The synthesis of the CD spiroketal fragment of spongistatin 1 (altohyrtin A) has been accomplished utilizing the addition of a metalated pyrone to an aldehyde and subsequent acid-catalyzed spirocyclization. A stereoselective hydrogenation and subsequent conformational inversion establish the C19 stereocenter and the axial-equatorial spiroketal center.

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Year:  2000        PMID： 10768196     DOI： 10.1021/ol005605e

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


  4 in total

1.  Polyketide assembly by alkene-alkyne reductive cross-coupling: spiroketals through the union of homoallylic alcohols.

Authors:  Daniel P Canterbury; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

2.  Development of an alkaloid-pyrone annulation: synthesis of pleiomaltinine.

Authors:  Robert E Ziegler; Shin-Jowl Tan; Toh-Seok Kam; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-15       Impact factor: 15.336

3.  Spongipyran Synthetic Studies. Total Synthesis of (+)-Spongistatin 2.

Authors:  Amos B Smith; Qiyan Lin; Victoria A Doughty; Linghang Zhuang; Mark D McBriar; Jeffrey K Kerns; Armen M Boldi; Noriaki Murase; William H Moser; Christopher S Brook; Clay S Bennett; Kiyoshi Nakayama; Masao Sobukawa; Robert E Lee Trout
Journal:  Tetrahedron       Date:  2009-08-15       Impact factor: 2.457

4.  A hetero-Diels-Alder approach to complex pyrones: an improved synthesis of the spongistatin AB spiroketal.

Authors:  Michael T Crimmins; Aaron C Smith
Journal:  Org Lett       Date:  2006-03-02       Impact factor: 6.005
  4 in total

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