A concise enantioselective total synthesis of rhizoxin D

A new and convergent synthesis of the antitumour macrolide rhizoxin D 2 is described. The synthesis features a Wadsworth–Emmons olefination and a facile intramolecular Stille reaction to elaborate the 16-membered macrocyclic core 5 from the vinyl iodide 3 and the vinyl stannane 4 as key steps. Graph...

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Bibliographic Details
Published inTetrahedron letters Vol. 43; no. 3; pp. 493 - 497
Main Authors Mitchell, Ian S., Pattenden, Gerald, Stonehouse, Jeffrey P.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.01.2002
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1ST TOTAL SYNTHESIS
SEGMENT
ADDITION-REACTIONS
C-C
MACROCYCLIC LACTONE ANTIBIOTICS
RHIZOPUS-CHINENSIS
STEREOSELECTIVE SYNTHESES
AGENT RHIZOXIN
C-C SUBUNITS
ANTITUMOR MACROLIDE RHIZOXIN
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Summary:A new and convergent synthesis of the antitumour macrolide rhizoxin D 2 is described. The synthesis features a Wadsworth–Emmons olefination and a facile intramolecular Stille reaction to elaborate the 16-membered macrocyclic core 5 from the vinyl iodide 3 and the vinyl stannane 4 as key steps. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)02154-2