Concise total synthesis of botryolide B

Synthesis and Biological Investigation of Δ12-Prostaglandin J3 (Δ12-PGJ3) Analogues and Related Compounds

“…Synthesis of Δ 12 -PGJ 3 Methyl Ester 2 and Lactone 11. In an effort to improve membrane permeability and stability, we synthesized the methyl ester (2) and lactone (11) derivatives of Δ 12 -PGJ 3 through the use of TMSCHN 2 (93% yield) and MNBA/DMAP (Shiina method, 6 71% yield), respectively, as summarized in Scheme 1. As will be discussed below, both the chemical stability and potency of derivatives 2 and 11 were improved over those of Δ 12 -PGJ 3 (1), providing motivation for further molecular designs along these structural types.…”

“…2.2. Synthesis of Δ 12 -PGJ 3 Ester (3−5 and 10), Amide Analogues (6−9) and Hydroxy Derivative 12. Ester derivatives of Δ 12 -PGJ 3 (i.e., 3−5 and 10, Scheme 2) were synthesized through their TBS−ether precursors (46−49, respectively) prepared from TBS−ether 45 2 by EDCI/DMAPfacilitated esterification as summarized in Scheme 2.…”

“…As described in a separate article 1 and a previous communication, 2 we developed a number of synthetic strategies for the synthesis of the reported antileukemic agent Δ 12 -prostaglandin J 3 (Δ 12 -PGJ 3 , 1, Figure 1). 3,4 In this article, we describe the application of these synthetic technologies for the synthesis of a series of designed analogues and derivatives of this newly discovered prostanoid whose biological profile 3,4 elevated it to a lead compound for drug discovery.…”

Recent topics of the stereodivergent synthesis of natural products

“…In addition to the lactonization by activation of hydroxycarboxylic acids, 8 transition metal-catalyzed addition reaction, 9 halo-and selenolactonization, 10 and ring-closing metathesis 11 have been reported as the synthetic methods for the five-or six-membered lactones. Breit and co-workers developed regio-and enantioselective rhodium-catalyzed addition of carboxylic acids to allenes in 2011.…”

Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of β-Substituted α-Oxobutyrolactones

“…Synthetic transformation of (−)- 2a was conducted. First, chiral silyl ether (+)- 3 was prepared according to the known synthetic procedure with tert -butyldimethylsilyl chloride (Scheme ), and the absolute configuration of (+)- 3 could be assigned as (3 R ,4 R ) by X-ray diffraction analysis (Scheme ). Thus, the absolute configuration of (−)- 2a was unambiguously assigned as (3 R ,4 R ).…”