A Convergent Synthesis of a Twelve‐Membered Macrolide Natural Product, (6 R ,12 S )‐6‐Hydroxy‐12‐methyl‐1‐oxacyclododecane‐2,5‐dione | Zendy

Radha Krishna Palakodety | Zendy; Kumar Pendyala Venkata Arun | Zendy

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A Convergent Synthesis of a Twelve‐Membered Macrolide Natural Product, (6 R ,12 S )‐6‐Hydroxy‐12‐methyl‐1‐oxacyclododecane‐2,5‐dione

Author(s) -

Radha Krishna Palakodety,

Kumar Pendyala Venkata Arun

Publication year - 2012

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.201200064

Subject(s) - chemistry , polyketide , natural product , stereochemistry , total synthesis , ring closing metathesis , metathesis , convergent synthesis , ring (chemistry) , organic chemistry , biosynthesis , polymerization , enzyme , polymer

A new polyketide metabolite, the twelve‐membered macrolide 1 , isolated from the endophytic fungal strain Cladosporium tenuissimum LR 463 of Maytenus hookeri , whose structure had been determined as (6 R ,12 S )‐6‐hydroxy‐12‐methyl‐1‐oxacyclododecane‐2,5‐dione, was synthesized for the first time by a convergent strategy via Yamaguchi esterification of 2 with 3 and ring‐closing metathesis (RCM) to afford the cyclic ester 1 that was eventually transformed to the target molecule. However, the total synthesis revealed that the assigned structure of the natural product is not correct.

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