Efficient and selective synthesis of siphonarienolone and related reduced polypropionates via Zr-catalyzed asymmetric carboalumination.
[reaction: see text] Siphonarienolone (1) has been synthesized from siphonarienal (3) in 66% over four steps. Synthesis of 3, in turn, has been achieved in two steps (85% combined yield) from 4, prepared from 3-buten-1-ol in seven steps (23% combined yield). Also, a two-step conversion of 3 into siphonarienone (2) is reported.
Magnin-Lachaux
Marina
M
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.
Tan
Ze
Z
Liang
Bo
B
Negishi
Ei-Ichi
E
D000473:Alkanes / Q000138:chemical synthesis*; D000535:Aluminum / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis*; D011422:Propionates / Q000737:chemistry*; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry*
D000473:Alkanes; D007659:Ketones; D011422:Propionates; C470331:siphonarienolone; D002244:Carbon; D015040:Zirconium; D000535:Aluminum