Stereoselective synthesis of spicigerolide

Tetrahedron Letters

Volumn 44, Issue 3, 2003, Pages 539-541

  Falomir, Eva ^a   Murga, Juan ^a   Carda, Miguel ^a   Marco, J Alberto ^b  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Asymmetric allylboration; Chiral pool; Ring closing metathesis; Spicigerolide

Indexed keywords

ALDEHYDE; LACTONE DERIVATIVE; RHAMNOSE; SPICIGEROLIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYTOTOXICITY; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0037433978     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02588-1     Document Type: Article

References (27)

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26. 13C NMR spectra identical to those of the original sample.
27. An alternative synthetic route was also investigated. Aldehyde 7 was subjected to Brown's allylation conditions to yield an 88:12 mixture of diastereoisomers in 88% yield. However, we experienced difficulties in the selective semihydrogenation of the triple bond of the obtained propargyl alcohol (competitive reduction of the C=C bond). We thus treated it with acryloyl chloride and subjected the acrylate to ring-closing metathesis to yield an alkynyl lactone. Here again, the selective semihydrogenation of the triple bond to yield 11 proved troublesome. In view of this, we discarded this route.