"One-Pot" Conversion of Carboxylic Acid Esters and Lactones to Olefinic Compounds

Absolute Configuration of Multifidene and Viridiene, the Sperm Releasing and Attracting Pheromones of Brown Algae

“…To give an impression of the operating dimensions: a gynogamete of the large sublitoral brown alga Laminaria digitata produces per min 10, OOO molecules of the specific hormone, 15 There are several reports on successful transformations of chiral olefines into alkanes without significant loss of optical activity using Pt/C as hydrogenation catalyst [16]. However, in our first attempts at ambient temperature massive scrambling of double bonds led to large amounts of trans-disubstituted products (cJ the Table).…”

Aluminum Acetals in Organic Synthesis

“…Less strained lactones tend to give slightly lower yields in this one‐pot sequence involving non‐stabilized ylides (Scheme ), whereas moderate yields (34–56 %) were obtained with esters and diesters 43…”

Large‐Scale Enantioselective Preparation of 2 E ,7 E , 5 S ,6 R , 5‐Hydroxy‐6‐methyl‐8‐phenyl‐octa‐2,7‐dienoic Acid, a Key Fragment for the Formal Total Synthesis of the Anti‐tumor Agent Cryptophycin 52

“…19 There have also been literature reports involving reduction of lactone with an equivalent of DIBAL and subsequent in situ reaction with Wittig reagents to afford styrenoid derivatives in decent yields. 20 These precedents paved the way for the implementation of a facile and efficient entry into trans styrenoid moieties and derivatives thereof. We envisioned a convergent approach (Scheme 3.3) involving DIBAL reduction of 21 and subsequent in situ reaction with the appropriate Wittig variant.…”