90741-73-4Relevant academic research and scientific papers
A Synthesis of C(16),C(18)-Bis-epi-cytochalasin D via Reformatsky Cyclization
Vedejs,Duncan
, p. 6073 - 6081 (2007/10/03)
Triene 5 has been prepared by the E-selective olefination of aldehyde 12 with the ylide 11. Several alternative syntheses of 12 were evaluated, and the successful route involved conversion of 22 into the vinyl ether 23 by Petasis olefination, followed by Claisen rearrangement. Diels-Alder cycloaddition of 5 with 4 gave the adduct 6 in 77% yield, and Reformatsky cyclization under dilution conditions afforded 10 (67%). After conversion to enol silane 32, oxidation with dimethyldioxirane produced 34. Conversion to a key intermediate 38 using electrophilic selenenylation and selenoxide rearrangement, followed by enolate alkylation and deprotection, gave 43. The X-ray crystal structure of 43 was determined to prove the stereochemistry.
Synthesis of cytochalasins: The route to sulfur-bridged [11] cytochalasans
Vedejs,Reid,Rodgers,Wittenberger
, p. 4351 - 4357 (2007/10/02)
The sulfur-mediated syntheses of the sulfur-bridged [11]cytochalasans 23 and 30 are described in full. Key steps include the highly selective Diels-Alder addition of 5a and 6 to give 7a, the generation and hetero-Diels-Alder trapping of the transient thio
