30346-21-5Relevant articles and documents
Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanolsviaa sequential reduction/C-H functionalization
Chen, Jun,Li, Chunyu,Lu, Ping,Shi, Zhan
, p. 10598 - 10604 (2021/08/20)
We report here a sequential enantioselective reduction/C-H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C-H silylation. Further transformations have been explored, including controllable regioselective ring-opening reactions. In addition, this strategy has been utilized for the synthesis of three natural products, phyllostoxin (proposed structure), grandisol and fragranol.
A highly stereocontrolled formal total synthesis of (±)- and of (-)-grandisol by 1,4-conjugated addition of organocopper reagents to cyclobutylidene derivatives
Bernard, Angela M.,Frongia, Angelo,Ollivier, Jean,Piras, Pier Paolo,Secci, Francesco,Spiga, Marco
, p. 4968 - 4974 (2008/02/01)
Starting from suitable cyclopropanes, a formal total synthesis of racemic grandisol and of the enantiopure (-)-grandisol is presented. The racemic synthesis of the grandisol precursor was accomplished in five steps. The synthesis of the chiral non-racemic precursor (1S,2S,2′R)-cis of this pheromone was realized in 10 steps, with an overall yield of 45%, using the enantiopure cyclobutanone (R,S), previously obtained by ring expansion of an optically pure oxaspiropentane. The key stereodefining step was the addition of lithium dimethylcuprate to a chiral α,β-unsaturated cyclobutylidene carbonyl derivative.
A new stereoselective synthesis of (±)-grandisol based on the remote alkylation protocol
Monteiro, Hugo J.,Stefani, Helio A.
, p. 2659 - 2663 (2007/10/03)
A new stereoselective synthesis of (±)-grandisol (1a) has been developed. The synthesis starts with a simple cyclobutyl derivative to which the methyl group and the 1,2-cis disposed side chains were appended through a remote alkylation protocol.
