Diversification of ortho-fused cycloocta-2,5-dien-1-one cores and 8 to 6-Ring conversion by sigma bond C-C cleavage

Diversification of ortho-fused cycloocta-2,5-dien-1-one cores and 8 to 6-Ring conversion by sigma bond C-C cleavage

Sequential treatment of 2-C6H4Br(CHO) with LiC≡CR1 (R1 = SiMe3, tBu), nBuLi, CuBr∙SMe2 and HC≡CCHClR2 [R2 = Ph, 4-CF3Ph, 3-CNPh, 4-(MeO2C)Ph] at -50 oC leads to formation of an intermediate carbanion (Z)-1,2-C6H4{CA(=O)C≡CBR1}{CH=CH(CH–)R2} (4). Low temperatures (-50 oC) favour attack at CB leading...

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Bibliographic Details
Main Authors: Eccleshare, Lee, Lozada-Rodriguez, Leticia, Cooper, Phillippa, Burroughs, Laurence, Ritchie, John, Lewis, William, Woodward, Simon
Format: Article
Published: Wiley-VCH Verlag 2016
Subjects:
Annulation
Medium-ring compounds
Synthetic methods
Ring expansion
C-C activation
Online Access:https://eprints.nottingham.ac.uk/34641/

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