An Enantioselective Total Synthesis of Natural (+)‐Luciduline | Zendy

Oppolzer Wolfgang | Zendy; Petrzilka Martin | Zendy

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An Enantioselective Total Synthesis of Natural (+)‐Luciduline

Author(s) -

Oppolzer Wolfgang,

Petrzilka Martin

Publication year - 1978

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19780610802

Subject(s) - chemistry , enantioselective synthesis , regioselectivity , intramolecular force , total synthesis , nitrone , yield (engineering) , sequence (biology) , stereochemistry , lycopodium , organic chemistry , catalysis , cycloaddition , biochemistry , materials science , metallurgy

The naturally occurring Lycopodium alkaloid (+)‐luciduline ( 1 ) has been synthesized from ( R )‐5‐methyl‐cyclohex‐2‐en‐1‐one ( 12 ) by a sequence of seven steps (s. Scheme 6 ) in 33% overall yield. The key step 4→6 presumably involves a transient nitrone 5 which undergoes a highly regioselective intramolecular addition to a non‐polarized olefinic bond.

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