Stereoselective total syntheses of (±)‐chanoclavine I and (±)‐isochanoclavine I by an intramolecular nitrone‐olefin/cycloaddition . Preliminary communication | Zendy

Oppolzer Wolfgang | Zendy; Grayson J. Ian | Zendy

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Stereoselective total syntheses of (±)‐chanoclavine I and (±)‐isochanoclavine I by an intramolecular nitrone‐olefin/cycloaddition . Preliminary communication

Author(s) -

Oppolzer Wolfgang,

Grayson J. Ian

Publication year - 1980

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.19800630639

Subject(s) - chemistry , nitrone , intramolecular force , stereoselectivity , cycloaddition , olefin fiber , stereochemistry , total synthesis , indole test , organic chemistry , catalysis

The racemic alkaloids chanoclavine I ( 1 ) and isochanoclavine I ( 2 ) have been synthesized stereoselectively from indole‐4‐carbaldehyde ( 3 ) by a sequence of 11 operations in overall yields of 14% and 2.4%, respectively. The key step 6 → 8 (Scheme 2) involves a transient nitrone 7 which undergoes a regio‐ and stereoselective intramolecular cycloaddition to a 1,2‐disubstituted olefinic bond.

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