Diverse reactivities of corey-chaykovsky ylides: Synthesis of 10-hydroxyaplysin

Synthetic Communications

Volumn 42, Issue 5, 2012, Pages 621-626

  Roy, Amalesh ^a   Venkateswaran, Ramanathapuram V ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

10 hydroxyaplysin; Corey Chaykovsky ylides; Methylene epoxide

Indexed keywords

10 HYDROXYAPLYSIN; EPOXIDE; KETONE DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DRUG SYNTHESIS; REDUCTION;

EID: 80755130363     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.528130     Document Type: Article

References (10)

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2. Yamamura, S.; Hirata, Y. Structures of aplysin and aplysinol, naturally occurring bromocompounds. Tetrahedron 1963, 19, 1485.
3. Biswas, S.; Ghosh, A.; Venkateswaran, R. V. Stereocontrolled synthesis of (±)-debromoaplysin, (±)-aplysin,(±)-debromoaplysinol, (±)-aplysinol, and (±)-isoaplysin. J. Org. Chem. 1990, 45, 3498
4. Yamamura, S.; Uemura, D.; Toda, M., Hirata, Y. Total synthesis of (±)aplysin and (±)debromoaplysin. Tetrahedron 1969, 25, 3509.
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6. Corey, E. J.; Chaykovsky, M. Dimethylsulfoxonium methylide; dimethylsulfonium methylide, a reagent for selective oxirane synthesis from aldehydes and ketones. J. Am. Chem. Soc. 1962, 84, 867, 3782.
7. Corey, E. J.; Chaykovsky, M. Dimethyloxosulfonium methylide (CH3)2SOCH2) and dimethylsulfonium methylide (CH3)2SCH2): Formation and application to organic synthesis. J. Am. Chem. Soc. 1965, 87, 1353
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10. The natural product was reported as a solid with m.p. 48-50°C Han et al.; Guo and Mao reported it as an oil.