Studies in marine macrolide synthesis: Synthesis of a fully functionalised C1-C28 subunit of spongistatin 1 (Altohyrtin A)

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8545-8548

  Paterson, Ian ^a   Wallace, Debra J ^a   Oballa, Renata M ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; PROTEIN SUBUNIT; SPONGISTATIN 1; UNCLASSIFIED DRUG;

DRUG SYNTHESIS; GROWTH INHIBITION; MICROTUBULE ASSEMBLY; MULTIDRUG RESISTANCE; NONHUMAN; OXIDATION; REVIEW; SPONGE (PORIFERA); STEREOCHEMISTRY;

PORIFERA;

EID: 0032512010     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01908-X     Document Type: Article

References (33)

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27. 8. Note that a boron-mediated aldol coupling was employed successfully in the Evans total synthesis of altohyrtin C (cf. ref 6c).
28. 13C NMR (100.6 MHz, CD3CN) δ 210.1, 170.5, 169.1, 169.0, 147.3, 130.7, 129.4, 113.6, 113.3, 98.2, 97.0, 95.1, 74.0 73.5, 73.1, 72.4, 70.5, 66.8, 66.3, 64.8, 64.4, 63.9, 60.6, 54.9, 54.6, 49.2, 47.6, 47.4, 45.0, 43.3, 42.4, 39.7, 38.1, 37.4, 36.9, 34.9, 34.8, 33.5, 31.3, 25.4, 20.8, 20.1, 18.7, 17.8, 13.0, 11.2, 10.7, 6.8, 6.5, -5.6, -5.7.
29. 10. Ireland, R. E.; Smith, M. G.; J. Am. Chem. Soc. 1988, 110, 854.
30. 11. Although selective removal of the secondary TBS ether in 8 could be achieved in moderate yield, in practice, it proved more efficient to remove both silicon protecting groups with aqueous HF and reintroduce the TIPS ether to give 9.
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32. iPrCHO) with negligible π-facial selectivity to give a mixture of predominantly two anti aldol products, indicating that a low level of substrate-based induction was attributable to the enolate component.
33. 14. While it has not proved possible to form MTPA esters of compound 18, NMR coupling constants, extensive model studies (cf. Scheme 3 and ref 4a) and the excellent NMR spectroscopic agreement of the derived acetate 19 (ref 9) with spongistatin 1 (1) allows for the confident assignment of the major isomer as the desired.