Asymmetric Total Synthesis of Pedrolide

The asymmetric total synthesis of pedrolide (>200 mg) with an unprecedented [5–5–5–6–6–3] hexacyclic core (pedrolane) was achieved. Its unique bicyclo[2.2.1]­heptane ring system was efficiently constructed via an enantioselective ene reaction of cyclopentadiene followed by a Wittig reaction, isom...

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Published inJournal of the American Chemical Society Vol. 146; no. 5; pp. 2928 - 2932
Main Authors Zhang, Wen, Yu, Peng-Cheng, Feng, Chen-Yun, Li, Chuang-Chuang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.02.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
DITERPENES
REAGENT
CYCLOADDITION
ENANTIOSELECTIVE SYNTHESIS
LEWIS-ACID
CROTYLATION
ALLYLATION
ALDEHYDES
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Summary:The asymmetric total synthesis of pedrolide (>200 mg) with an unprecedented [5–5–5–6–6–3] hexacyclic core (pedrolane) was achieved. Its unique bicyclo[2.2.1]­heptane ring system was efficiently constructed via an enantioselective ene reaction of cyclopentadiene followed by a Wittig reaction, isomerization, and a diastereoselective intramolecular Diels–Alder reaction cascade. The highly oxygenated carane [6–3] ring system was synthesized via a ring-closing metathesis reaction followed by an unusual free carbene cyclopropanation. Furthermore, the 12 contiguous stereocenters of pedrolide were installed diastereoselectively.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.3c14150