Total synthesis of siphonarin B and dihydrosiphonarin B

Organic Letters

Volumn 4, Issue 3, 2002, Pages 391-394

  Paterson, Ian ^a   Chen, David Yu Kai ^a   Franklin, Alison S ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; SIPHONARIN B; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS;

KETONES; MOLECULAR STRUCTURE; SPIRO COMPOUNDS;

EID: 0037034362     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017082w     Document Type: Article

References (30)

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25. The configuration was determined by NMR analysis of the derived PMP acetal obtained on exposure of 22 to anhydrous DDQ.
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29. Due to the small quantity of dihydrosiphonarin prepared, an accurate specific rotation could not be measured.
30. Siphonarin B (2) was obtained in 25 steps (0.9% overall yield) from (S)-3-(benzyloxy)-2-methylpropanal (ref 5a). The low yield obtained for the final step is due to competing decomposition encountered under the prolonged reaction time (16 h) needed to remove the PMB ether.