Synthesis of precursors of phomactins using [2,3]-Wittig rearrangements

Tetrahedron

Volumn 65, Issue 21, 2009, Pages 4201-4211

  Shapland, Peter D P ^a   Thomas, Eric J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; HYDROXYL GROUP; LITHIUM DIMETHYLCUPRATE; PHOMACTIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMISTRY; EPOXIDATION; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; WITTIG REARRANGEMENT; X RAY CRYSTALLOGRAPHY;

EID: 64649100805     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.031     Document Type: Article

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46. On the basis of steric interactions between the alkynyl group and the acetal in the transition state for the [2,3]-Wittig rearrangements, it is suggested that the two products were diastereoisomers 26a and 26b. This is consistent with the formation of two diastereomeric products from the rearrangement of acetal 33 and the formation of three products from the rearrangement of the protected alcohol 44. Moreover, the major product isolated from a [2,3]-Wittig rearrangement of an analogous albeit slightly more complex system en route to the phomactin nucleus was shown to have the relative configuration at C(2) and C(1′) as shown here for products 26a and 26b (see Ref. 16).{A figure is presented}
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48. 3 for the minor ketone 35a suggested that this had the structure shown below. The major rearrangement product was therefore provisionally assigned as alcohol 34b. This assignment was not confirmed in this series but is consistent with results obtained later for analogous systems (see Ref. 18).{A figure is presented}
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