[2 + 2] cycloaddition of optically active ketenes. Synthesis of (−)‐blastmycinone . Preliminary Communication | Zendy

Fráter Georg | Zendy; Müller Urs | Zendy; Günther Wulf | Zendy

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[2 + 2] cycloaddition of optically active ketenes. Synthesis of (−)‐blastmycinone . Preliminary Communication

Author(s) -

Fráter Georg,

Müller Urs,

Günther Wulf

Publication year - 1986

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.19860690813

Subject(s) - chemistry , cycloaddition , ether , adduct , optically active , stereochemistry , selectivity , transformation (genetics) , propenyl , sequence (biology) , medicinal chemistry , organic chemistry , catalysis , biochemistry , gene

[2 + 2] Cycloaddition of (menthyloxy)methylketene ( 2 ) to cis ‐ethyl propenyl ether showed a ca. 3:1 diastereo‐selectivity. A two‐step transformation of the thermodynamically more stable adduct 4 furnished the (2 R *, 3 R *)‐compound 5 with ca. 50% e.e. ( Scheme 1 ). The analogous reaction sequence with cis ‐ benzyl 1‐hexenyl ether ( 9 ) and 2 showed a ca. 5:1 diastereoselectivity in 10 and 11 ( Scheme 2 ). Absolute configuration of C(3) and C(4) in 11 has been proved by converting it to (−)‐blastmycinone. Accordingly, the preferred transition state has been deduced as 15 .

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