Asymmetric synthesis of passifloricin A: A correction in structure

Tetrahedron Letters

Volumn 44, Issue 43, 2003, Pages 7909-7912

  Murga, Juan ^a   García Fortanet, Jorge ^a   Carda, Miguel ^a   Marco, J Alberto ^b  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Asymmetric allylboration; Lactones; Passifloricin A; Ring closing metathesis

Indexed keywords

ANTINEOPLASTIC AGENT; LACTONE DERIVATIVE; PASSIFLORICIN A; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 0141648293     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.007     Document Type: Article

References (21)

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12. After our communication (Ref. 6) had appeared, a second report on the synthesis of the same two compounds was published: BouzBouz, S.; Cossy, J. Tetrahedron Lett. 2003, 44, 4471-4473. The retrosynthetic concept used by these authors is identical in its essence to our own, except for the use of chiral allyltitanium reagents instead of allylboranes.
13. These were the two following stereoisomers: The second one is the enantiomer of a natural lactone isolated from Eupatorium pilosum (Herz, W.; Ramakrishnan, G. Phytochemistry 1978, 17, 1327-1332). The spectral properties of the synthetic compound were found to be identical with those published for the natural product. Their optical rotations showed obviously opposite signs (unpublished results).
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18. Details of the synthesis of compounds 3a-d and evaluation of their cytotoxic properties will be reported in due course. This work is part of the projected Ph.D. thesis of J.G.-F.
19. Freshly prepared by PCC oxidation of n-pentadecanol.
20. 3 solution, where the natural product is more soluble. The synthetic and the natural product were then found to have almost identical optical rotations.
21. 3) for a sample of natural passifloricin A. The NMR spectra of synthetic 3b are identical to those of the natural sample and to those of a mixture of natural and synthetic compound.