New synthetic approaches to the oxahydrindane subunit of avermectins

Tetrahedron

Volumn 53, Issue 14, 1997, Pages 5195-5216

  Morelli, Jean François ^a   Pouilhès, Annie ^a   Langlois, Yves ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AVERMECTIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0030906040     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00182-8     Document Type: Article

References (30)

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15. For a related fragmentation reaction, see: Campbell, M. C.; Sainsbury, M.; Searle, P. A. Tetrahedron Lett., 1992, 33, 3181-3184.
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17. 2.
18. Examination of coupling constant C4H-C5H J= 11 Hz in compound 13 let us to attribute trans configurations at the ring junction and the absolute configurations at C3 and C4 in diols 11 and 12.
19. For synthetic facilities, this sequence of reactions was performed on racemic compounds. Racemic isoquinuclidine derivatives 9a-9c were prepared according: Raucher, S.; Lawrence, R. F. J. Am. Chem. Soc., 1987, 109, 442-446.
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23. 10% of the corresponding nitrate at C3 was also obtained in this reaction.
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25. a) see reference 3c.
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27. The previously observed base induced fragmentation was not possible with acetonide 29. The C-N bond in that case is not in an allylic position like in compounds 9a-9b.
28. 2O. THF affording a compound identical with the cis diol 12.
29. Avermectin numbering.
30. These two strategies afforded cis diols 11 or 31 of reverse absolute configurations at C3 and C4 if (+)-camphor is used as chiral auxiliary. In a total synthesis of Avermectin antibiotics, the use of (+) or (-)-camphor will allow the control of absolute configuration in both cases.