Portal de Periódicos da CAPES

Total Synthesis of the Neotropical Poison-Frog Alkaloid (−)-205B

2005; American Chemical Society; Volume: 7; Issue: 15 Linguagem: Inglês

10.1021/ol0510264

1523-7060

Amos B. Smith, Dae‐Shik Kim,

Microbial Natural Products and Biosynthesis

A stereocontrolled total synthesis of the neotropical poison-frog alkaloid (−)-205B (1) has been achieved, employing a dithiane three-component linchpin coupling, a one-pot sequential construction of the embedded indolizidine ring, and ring-closing metathesis (RCM) to arrive at the novel 8b-azaacenaphthylene ring system comprising the alkaloid. The synthesis proceeded with a longest linear sequence of 19 steps, affording (−)-1 in 5.6% overall yield.