A highly convergent approach toward (-)-brevenal.
Progress toward a highly convergent, asymmetric synthesis of brevenal is reported. Construction of the AB-ring and E-ring cyclic ether fragments was achieved through asymmetric alkylation/ring-closing metathesis strategies. A Horner-Wadsworth-Emmons olefination was used in a key bond-forming step to couple the advanced cyclic fragments and enable rapid access to the AB-E ring system.
Crimmins
Michael T
MT
Kenan and Caudill Laboratories of Chemistry, University of North Carolina at Chapel Hill, North Carolina 27599, USA. crimmins@email.unc.edu
Shamszad
Mariam
M
Mattson
Anita E
AE
D000478:Alkylation; D002384:Catalysis; D004141:Dinoflagellida / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008387:Marine Toxins / Q000302:isolation & purification / Q000633:toxicity; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D004987:Ethers; D008387:Marine Toxins; D011108:Polymers; C489035:brevenal (polyether)
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