Total Synthesis of Pseudotrienic Acid B: A Bioactive Metabolite from Pseudomonas sp. MF 381‐IODS

Abstract

Acid advancement: An efficient and highly convergent stereoselective synthesis of pseudotrienic acid B (see structure) has been achieved. Synthetic highlights include a crotyltitanation reaction to control the stereogenic centers at C11 and C20, a cross‐metathesis reaction to synthesize the triene moiety, and a Stille cross‐coupling reaction to complete the assembly of the carbon framework of the natural product.

Total Synthesis of (−)-Fusarisetin A and Reassignment of the Absolute Configuration of Its Natural Counterpart

“…Based on the above analysis, we first investigated the preparation of trans -decalin 7 employing an intramolecular D-A reaction as the key transformation, − as shown in Scheme . Starting with aldehyde 9 , which is readily prepared from (−)-citronellal or (−)-citronellol, we carried out H-W-E reaction with lithiated phosphonate 10 . Reduction with DIBAL-H and acetylation of the resulting primary alcohol led to triene 12 with good overall efficiency (67%, 3 steps).…”

Bio‐Inspired Formal Synthesis of Hirsutellones A–C Featuring an Electrophilic Cyclization Triggered by Remote Lewis Acid‐Activation

“…Starting from ( R )‐(+)‐citronellal ( 10 ), the trienoate 11 was readily constructed in 74 % yield by a Horner–Wadsworth–Emmons (HWE) reaction with the deprotonated 6‐phosphonohexa‐2,4‐dienoate 12 (Scheme ) 11. Taking advantage of the electron‐deficiency of 11 , the trisubstituted double bond was selectively dihydroxylated in the presence of OsO 4 and N ‐methylmorpholine‐ N ‐oxide (NMO), giving the diol 13 in 83 % yield (based on recovered starting material, b.r.s.m.)…”

Total Synthesis of Bistramide A and Its 36(Z) Isomers: Differential Effect on Cell Division, Differentiation, and Apoptosis

“…by using TADDOL instead as a chiral ligand (Scheme ). The first step consists of the formation of chiral amino alcohol 36 by asymmetric crotyltitanation 25. 26 The amino alcohol was protected as a 1,3‐oxazolidine and cleavage of the double bond with ruthenium(III) chloride/sodium periodate provided amino acid 37 , which was fully deprotected under acidic conditions.…”