Total Synthesis of (−)-Sessilifoliamide J

Abstract

An efficient synthesis of the Stemona alkaloid (-)-sessilifoliamide J (1) in 12 steps and 7.7% overall yield from the known building block 8 is presented. The synthesis features the Corey lactonization reaction and a highly diastereoselective α-methylation reaction to build the spiro-lactone moiety.

Towards stereochemical control: A short formal enantioselective total synthesis of pumiliotoxins 251D and 237A

“…In recent years, we have been engaged in the development of efficient methodologies for the synthesis of nitrogen-containing bioactive heterocycles [33–37], and recently reported an approach for the synthesis of (8 R ,8a S )-8-hydroxy-5-indolizidinone ( 6 ) [38]. As a continuation of that study, the synthesis of (8 S ,8a S )- 5 starting from compound 6 was envisioned.…”

Recent Advances in Metal‐Catalyzed Bond‐Forming Reactions of Ketene S,S‐Acetals

“…Di‐coupling products 78 are obtained through an initial interconversion of ( E )‐ 77 to ( Z )‐ 77 and a similar cross‐coupling process (Scheme ) . This coupling method was then successfully applied by us for the synthesis of coumestan derivatives …”

Ring strain strategy for the control of regioselectivity. Gold-catalyzed anti-Markovnikov cycloisomerization initiated tandem reactions of alkynes

“…The skeleton of c-Lactone is found in a variety of bioactive natural products as a core structural element [16][17][18][19][20][21][22][23]. In addition, c-Lactones have also proven to be the vital precursors for the construction of many biologically active compounds and natural products [24][25][26][27][28][29][30].…”