Syntheses of (+)‐( S , S )‐( cis ‐6‐Methyltetrahydropyran‐2‐yl)acetic acid and of (−)‐( R , R )‐Didesoxy‐pyrenophorine Using a New d 5 ‐Reagent  . Preliminary communication | Zendy

Seebach Dieter | Zendy; Phmakotr Manat | Zendy

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Syntheses of (+)‐( S , S )‐( cis ‐6‐Methyltetrahydropyran‐2‐yl)acetic acid and of (−)‐( R , R )‐Didesoxy‐pyrenophorine Using a New d 5 ‐Reagent . Preliminary communication

Author(s) -

Seebach Dieter,

Phmakotr Manat

Publication year - 1979

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.19790620322

Subject(s) - chemistry , synthon , reagent , nucleophile , epoxide , derivative (finance) , beckmann rearrangement , acetic acid , ring (chemistry) , stereochemistry , hydrolysis , lactone , combinatorial chemistry , organic chemistry , oxime , financial economics , economics , catalysis

The Li/K‐derivative 6 is used to synthesize the title compounds ( 3a and 4a ) in enantiomerically pure form from (−)‐( S )‐propylene epoxide. The C,C bond forming key step leading to the hydroxyketone 7 is followed by cyclization (→, 8 ), Beckmann cleavage (→ 9b ) and hydrolysis to 3a (recently isolated from civet). Base treatment of 3a opens the ring ( 10 ) to give the hydroxyacid 1 which is cyclized to the macrolide 4a . The synthetic usefulness of the highly nucleophilic doubly reduced dienone system 6 as d 5 ‐reagent (see synthons 2) is thus demonstirated.

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