A facile approach for the total synthesis of neurotrophic diyne tetraol petrosiol A and petrosiol E

Marine natural products

“…511 A large number of rst syntheses have been reported in 2016, including vesparioside B, 512,513 strongylodiols C and D, 514,515 lembehyne B, 516,517 the previously unreported xestospongenyne, 518 and petrosiol A. 519,520 The relative conguration of the C-13-C-25 section of hemicalide 1003 (ref. 521) has been determined by synthesis.…”

Photocatalytic Umpolung ofN- andO-substituted alkenes for the synthesis of 1,2-amino alcohols and diols

“…7,8 1-Alkynyl-1,2-diols can be found, for example, in the Petrosiol family of neurotrophic diyne tetraols. 9,10 Enamides and ene-carbamates are versatile starting materials for the generation of complex aminated building blocks. [11][12][13][14][15][16] In particular, they have been used extensively in atom transfer radical addition (ATRA) reactions.…”

Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I

“…Thus, the mixture of 25 and 25a was oxidized under Dess–Martin conditions to give the prochiral ene–yne–one 17 in 87% yield. The ketone 17 was then subjected to a stereoselective asymmetric reduction [ 23 , 29 – 31 ] in the presence of ( S )-CBS as the catalyst to yield the chiral propargylic alcohol 25 with 92% ee ( Scheme 3 ) [ 32 ].…”

“…In continuation to our research interest on the synthesis of acetylenic compounds [ 19 – 21 ], recently we have accomplished the total synthesis of the diacetylenic polyol natural products petrosiols A, D, E ( 11 , 12 , 13 ) [ 22 – 23 ] and strongylodiols A–D ( 1 – 4 ) [ 24 ]. Herein we describe the total synthesis of strongylodiols H and I ( 9 and 10 ).…”