About this item
- Title
- Enantioselective Synthesis of an Analogue of Nanaomycin A
- Content partner
- The University of Auckland Library
- Collection
- ResearchSpace@Auckland
- Description
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 delive...
- Format
- Research paper
- Research format
- Journal article
- Date created
- 2007
- Creator
- Brimble, Margaret / Bachu, P / Sperry, Jonathan
- URL
- https://hdl.handle.net/2292/8100
- Related subjects
- pyranonaphthoquinone antibiotics / nanaomycin A / asymmetric allylation / intramolecular cyclization / CATALYTIC ASYMMETRIC ALLYLATION / CHIRAL INDIUM(III) COMPLEX / PYRANONAPHTHOQUINONE ANTIBIOTICS / HOMOALLYLIC ALCOHOLS / METHYL-ESTER / ALDEHYDES / ALLYLBORATION / ORGANOBORANES / OXIDATION / OLEFINS
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