Expedient Enantioselective Synthesis of Cermizine D

An efficient enantioselective synthesis of cermizine D has been developed that exploits the use of a common intermediate to access over 85% of the carbon backbone. Key steps include an organocatalyzed heteroatom Michael addition, a diastereoselective alkylation with α-iodomethyl phenyl sulfide, a co...

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Veröffentlicht in:	Organic letters 2012-03, Vol.14 (6), p.1596-1599
Hauptverfasser:	Veerasamy, Nagarathanam, Carlson, Erik C, Carter, Rich G
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Alkaloids - chemistry Alkylation carbon Catalysis chemical structure Cyclization desulfurization diastereoselectivity enantioselective synthesis Lycopodium - chemistry Molecular Structure organic compounds Quinolizidines - chemical synthesis Quinolizidines - chemistry Stereoisomerism sulfides Sulfones - chemistry
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Beschreibung
Zusammenfassung:	An efficient enantioselective synthesis of cermizine D has been developed that exploits the use of a common intermediate to access over 85% of the carbon backbone. Key steps include an organocatalyzed heteroatom Michael addition, a diastereoselective alkylation with α-iodomethyl phenyl sulfide, a conjugate addition to a vinyl sulfone species, and a sulfone coupling/desulfurization sequence to join the two major subunits.
ISSN:	1523-7060 1523-7052 1523-7052
DOI:	10.1021/ol300342n