Stereoselective Total Synthesis of the Natural (+)-Lasonolide A

Stereoselective Total Synthesis of the Natural (+)-Lasonolide A

ABSTRACT The natural (+)-lasonolide A (1), an anti-tumor agent, has been synthesized via thermodynamic benzylidene formation at the C 22 quaternary chiral center, use of a disulfone equivalent for elongation of the C 15 -C 17 three-carbon chain as well as introduction of the two TRANS olefins at C 1...

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Veröffentlicht in:Synthesis (Stuttgart) 2004-05, Vol.2004 (7), p.1102-1114
Hauptverfasser: Kang, Sung Ho, Kang, Suk Youn, Choi, Hyeong-wook, Kim, Chul Min, Jun, Hyuk-Sang, Youn, Joo-Hack
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Sprache:eng
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Zusammenfassung:ABSTRACT The natural (+)-lasonolide A (1), an anti-tumor agent, has been synthesized via thermodynamic benzylidene formation at the C 22 quaternary chiral center, use of a disulfone equivalent for elongation of the C 15 -C 17 three-carbon chain as well as introduction of the two TRANS olefins at C 15 and C 17 , iodocyclization for the upper THP, Michael addition for the bottom THP, and intramolecular Horner-Emmons olefination for the 20-membered macrolactone.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2004-822340