Enantioselective synthesis of an analogue of nanaomycin A

Brimble, M. A., Bachu, P. and Sperry, J. (2007) Enantioselective synthesis of an analogue of nanaomycin A. Synthesis, 18: 2887-2893. doi:10.1055/s-2007-983848

Author Brimble, M. A.
Bachu, P.
Sperry, J.
Title Enantioselective synthesis of an analogue of nanaomycin A
Journal name Synthesis   Check publisher's open access policy
ISSN 0039-7881; 437-210X
Publication date 2007-09
Sub-type Article (original research)
DOI 10.1055/s-2007-983848
Issue 18
Start page 2887
End page 2893
Total pages 7
Place of publication Stuttgart, Germany
Publisher Georg Thieme Verlag
Language eng
Formatted 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).
Keyword Pyranonaphthoquinone antibiotics
Nanaomycin A
Asymmetric allylation
Intramolecular cyclization
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Institute for Molecular Bioscience - Publications
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Citation counts: TR Web of Science Citation Count  Cited 14 times in Thomson Reuters Web of Science Article | Citations
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Created: Tue, 20 Mar 2012, 15:16:16 EST by Susan Allen on behalf of Institute for Molecular Bioscience