Synthesis of (−)-Okilactomycin by a Prins-Type Fragment-Assembly Strategy

Synthesis of (−)-Okilactomycin by a Prins-Type Fragment-Assembly Strategy

All things converge: A highly convergent synthesis of (−)‐okilactomycin utilizes a Prins‐type Maitland–Japp cyclization for the fragment assembly of two complex intermediates (see scheme). The synthesis also employs a highly diastereoselective Lewis acid promoted Diels–Alder reaction and an olefin r...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-06, Vol.50 (26), p.5892-5895
Hauptverfasser: Tenenbaum, Jason M., Morris, William J., Custar, Daniel W., Scheidt, Karl A.
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemistry
Cyclization
Lactones - chemical synthesis
Lactones - chemistry
Maitland-Japp reaction
natural products
Prins reaction
Pyrans - chemistry
Stereoisomerism
tetrahydropyrans
total synthesis
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Zusammenfassung:All things converge: A highly convergent synthesis of (−)‐okilactomycin utilizes a Prins‐type Maitland–Japp cyclization for the fragment assembly of two complex intermediates (see scheme). The synthesis also employs a highly diastereoselective Lewis acid promoted Diels–Alder reaction and an olefin ring‐closing metathesis to close a strained 11‐membered macrocycle.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201102037