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. 2010 Nov 15;49(47):8860-3.
doi: 10.1002/anie.201004911.

A simple and general platform for generating stereochemically complex polyene frameworks by iterative cross-coupling

Suk Joong Lee  1 , Thomas M Anderson, Martin D Burke
Affiliations

A simple and general platform for generating stereochemically complex polyene frameworks by iterative cross-coupling

Suk Joong Lee et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Scheme 1
Scheme 1
Polyene natural products derived from a wide range of biosynthetic pathways.
Scheme 2
Scheme 2
A) A strategy for ICC of halogen-masked bifunctional building blocks. B) Core building blocks to enable general access to stereoisomeric iodopolyenyl MIDA boronates. C) New iodopolyenyl MIDA boronates for the synthesis of polyene natural products.
Scheme 3
Scheme 3
Synthesis of bifunctional MIDA boronate building blocks (E)-1 and (Z)-1 from the common intermediate ethynyl MIDA boronate 6. Color code: red, O; gray, C; green, H; yellow, B; light blue, N; dark blue, I. DMSO=dimethyl sulfoxide, AIBN=azobisisobutyronitrile, NIS=N-iodosuccinimide, PADC=potassium azodicarboxylate.
Scheme 4
Scheme 4
The stereocontrolled preparation of (Z)-2.
Scheme 5
Scheme 5
Efficient and stereospecific syntheses of all possible stereoisomers of 3 by metal-selective ICC. TC=thiophene-2-carboxylate.
Scheme 6
Scheme 6
Preparation of iodotrienyl MIDA boronate (E,E,E)-4 by metal-selective ICC.
Scheme 7
Scheme 7
Synthesis of the stereochemically complex heptaene core of vacidin A.
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References

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