Tomas Hudlicky

TL;DR: Trant et al. as mentioned in this paper used a d-chiro-inositol derivative as a chiral tether to facilitate the regio-,diastereo-, and enatioselective cycloaddition between cinnamic acid and hexa-3,5-dienoic acid.

TL;DR: The Burgess reagent has been used primarily for the dehy-dration of secondary and tertiary alcohols, and its use has figured in the total synthesis of important natural prod- ucts, for example in Rigby's syntheses of narciclasine 3 and cedrene, 4 Nicolaou's synthesis of efrotomycin, 5 Uskokovic's synthesis, 6 and Holton's syn- thesis of Taxol ® as discussed by the authors.

Abstract: The first total synthesis of polyhydroxylated cyclohexenone 1, isolated from Pleiogynium timorense and named pleiogenone A, is reported that also serves as a proof of structure and absolute configuration. Enzymatic dihydroxylation of benzoic acid with R. eutrophus B9 provided enantiomerically pure diene diol 6. Elaboration of the carboxylate moiety to the alkyl side chain was followed by singlet oxygen cycloaddition to furnish an endoperoxide whose reduction with thiourea led to cyclitol 19. Several protective operations were required before oxidation and the final extension of the side chain by a Wittig reaction. After final deprotection of the acetonide functionality the desired pleiogenone A (1) was obtained in 14 operations from benzoic acid.

TL;DR: In this paper, the authors present novel pancratistatins and methods for their total asymmetric synthesis, including (+)-pancratistatin, (+)-7-deoxypancratistsatin, (-)-7deoxyclic 7-deoxy-polycyclic pancratists, truncated truncated pancreatistatists, and related derivatives.