A new strategy for cyclopentenone synthesis.
[reaction--see text] A new strategy for the synthesis of 2,3-disubstituted cyclopentenones emerges from two key reactions-the ruthenium-catalyzed three-component coupling of an equivalent of HBr, an alkyne, and a vinyl ketone and the Ni-Cr Barbier type reaction. As a result, these important structures are readily accessed from an alkyne and a vinyl ketone (which derive directly from carboxylic acids). Syntheses of tetrahydrodicranenone B and rosaprostol illustrate the new strategy.
Trost
B M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@leland.stanford.edu
Pinkerton
A B
AB
D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry; D000897:Anti-Ulcer Agents / Q000138:chemical synthesis / Q000737:chemistry; D000959:Antihypertensive Agents / Q000138:chemical synthesis / Q000737:chemistry; D019068:Bryopsida / Q000737:chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D005100:Expectorants / Q000138:chemical synthesis / Q000737:chemistry; D005765:Gastrointestinal Agents / Q000138:chemical synthesis / Q000737:chemistry; D011465:Prostaglandins, Synthetic / Q000138:chemical synthesis / Q000737:chemistry; D011466:Prostanoic Acids / Q000138:chemical synthesis / Q000737:chemistry
D000890:Anti-Infective Agents; D000897:Anti-Ulcer Agents; D000959:Antihypertensive Agents; D003517:Cyclopentanes; D004952:Esters; D005100:Expectorants; D005765:Gastrointestinal Agents; D011465:Prostaglandins, Synthetic; D011466:Prostanoic Acids; C410206:tetrahydrodicranenone B; C013905:cyclopentenone; C035288:rosaprostol