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Synthesis 2007(18): 2887-2893
DOI: 10.1055/s-2007-983848
DOI: 10.1055/s-2007-983848
PAPER
© Georg Thieme Verlag Stuttgart · New York
Enantioselective Synthesis of an Analogue of Nanaomycin A
Weitere Informationen
Received
30 May 2007
Publikationsdatum:
08. August 2007 (online)
Publikationsverlauf
Publikationsdatum:
08. August 2007 (online)
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Abstract
The enantioselective synthesis of (1R,3R)-deoxynanaomycin A (4) is reported. The key step involves introduction of the stereocenter in (S)-homoallylic alcohol 10a using an asymmetric allylation of aldehyde 9. Lithium-halogen exchange of bromo acetate 11 triggered rapid intramolecular cyclization furnishing lactol 12 that underwent silane-mediated reduction providing (1R,3S)-naphthopyran 13. Dihydroxylation and oxidative cleavage gave aldehyde 15 that underwent two successive oxidations delivering (1R,3R)-deoxynanaomycin A (4) in high enantiopurity and an overall 7% yield over 12 steps from 1-naphthol (5).
Key words
pyranonaphthoquinone antibiotics - nanaomycin A - asymmetric allylation - intramolecular cyclization
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