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Synthesis of the aryltetralin lignan skeleton via the Prins reaction

✍ Scribed by Snider, Barry B.; Jackson, Andrew C.

Book ID
120259461
Publisher
American Chemical Society
Year
1983
Tongue
English
Weight
571 KB
Volume
48
Category
Article
ISSN
0022-3263

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Advances in the Synthesis of Aryltetrali
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## Abstract Etoposide and tenoposide, derivatives of the aryltetralin lignan lactone podophyllotoxin (**5**), are clinically important anticancer agents. The structure of podophyllotoxin includes four contiguous chiral centres contained within a stereochemically unstable __trans__‐fused tetrahydron

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A new Pd-catalyzed route to (Β±)-podophyllotoxin is disclosed. The strategy is based on an efficient organoaqueous reaction that diastereoselectively introduces the C-4 hydroxyl group and the furan ring. Further functionalization led to an iododerivative, which was cyclized under optimized conditions