The enantioselective total synthesis of laurendecumallene B

Abstract

Use of two key reactions initiated by BDSB (Et2SBr·SbCl5Br) affords an efficient total synthesis of laurendecumallene B, establishing the configuration of its two bromine-bearing stereocenters.

Marine natural products

“…408,409 The total synthesis of laurendecumallene B has been achieved. 410 The biomimetic total synthesis of laurefurenynes C-F 921-924 has necessitated their structural revision as shown. 411 Reviews of relevance to the Rhodophyta include a summary of bioactive red algal oxylipins, 412 a summation of the impact of seaweeds (primarily Rhodophyta) on enteric methane production in ruminants, 413 and an assessment of the nutraceutical value of red algae and their metabolites.…”

Catalytic Asymmetric Conjugate Addition/Hydroalkoxylation Sequence: Expeditious Access to Enantioenriched Eight-Membered Cyclic Ether Derivatives

“… Accordingly, over the past decades, the asymmetric synthesis of eight-membered cyclic ethers has caused considerable attention, and varieties of synthetic strategies have been designed for the construction of such a structure. Representative approaches toward these scaffolds include ring expansions, ring-closing metathesis, retro-Claisen rearrangement, intramolecular alkylation, and others . However, the application of these methods has been limited by their unsatisfactory yields, costly catalysts, multistep synthesis, and poor stereoselectivities.…”

Asymmetric Total Synthesis of Amphirionin-2

“…Alcohol 7 was then reacted with 1-phenyl-1 H -tetrazole-5-thiol (PTSH) in the presence of Ph 3 P/DIAD following the Mitsunobu protocol to produce the corresponding sulfide, which was further oxidized to sulfone 8 using mCPBA. On the other hand, the known alcohol 9 , obtained from R -glycidyl benzyl ether in one step following the literature procedure, was treated with TESCl/Et 3 N, followed by OsO 4 /NMO and NaIO 4 /NaHCO 3 to obtain the required aldehyde 10 . The stage was set for Julia–Kocienski olefination to couple aldehyde 10 and sulfone 8 .…”