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

Authors
Crimmins, MT Katz, JD
Citation
Mt. Crimmins et Jd. Katz, Synthesis of the C16-C28 spiroketal subunit of spongistatin 1 (altohyrtin A): The pyrone approach, ORG LETT, 2(7), 2000, pp. 957-960
Citations number
42
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
7
Year of publication
2000
Pages
957 - 960
Database
ISI
SICI code
1523-7060(20000406)2:7<957:SOTCSS>2.0.ZU;2-0
Abstract
[GRAPHICS] 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 ste reocenter and the axial-equatorial spiroketal center.