Stereoselective total synthesis of (-)-9-deoxygoniopypyrone

Synlett

Volumn , Issue 7, 2007, Pages 1112-1114

  Prasad, Kavirayani R ^a   Dhaware, Madhuri G ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

( ) 9 deoxygoniopypyrone; Stereoselective reduction; Styryllactone; Tartaric acid

Indexed keywords

9 DEOXYGONIOPYPYRONE; AMIDE; GAMMA HYDROXYBUTYRAMIDE; PYRONE DERIVATIVE; TARTARIC ACID; UNCLASSIFIED DRUG;

ALLYLATION; ANNONACEAE; ARTICLE; CYCLIZATION; DIELS ALDER REACTION; DIHYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; GONIOTHALAMUS GIGANTEUS; STEREOCHEMISTRY;

EID: 34248227311     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-973873     Document Type: Article

References (14)

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13. To circumvent the use of expensive Grubbs' second-generation catalyst in the synthesis of lactone 14, an alternate route for 14 from alcohol 12 was examined. As shown below (Scheme 4), homoallylic alcohol 12 was protected as its allyl ether, which underwent smooth RCM reaction with Grubbs' first generation catalyst to yield the dihydropyran 15 in 90% yield. PCC oxidation of the dihydropyran 15 resulted in the lactone 14 in 44% yield (72% based on recovered starting material). (Chemical Equation Presented)
14. 4: 297.1105; found: 297.1103.