Pseudo-domino palladium-catalyzed allylic alkylation/Mizoroki-Heck coupling reaction: a key sequence toward (±)-podophyllotoxin

Tetrahedron Letters

Volumn 49, Issue 5, 2008, Pages 760-763

  Mingoia, Francesco ^a   Vitale, Maxime ^b   Madec, David ^b   Prestat, Guillaume ^b   Poli, Giovanni ^b  

^a CNR   (Italy)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

Catalysis; Domino; Palladium; Podophyllotoxin; Ring closure

Indexed keywords

PALLADIUM; PODOPHYLLOTOXIN;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 37649009484     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.202     Document Type: Article

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55. 3, 100 MHz): 48.6, 52.9, 56.2, 57.1, 60.8, 101.9, 104.7, 107.3, 113.3, 115.1, 133.3, 135.7, 137.0, 147.2, 147.7, 153.2, 167.5.
56. 3, 100 MHz): 40.5, 52.1, 52.3, 52.9, 56.0, 60.7, 63.4, 101.8, 107.3, 109.4, 113.0, 116.7, 119.1, 132.4, 132.6, 134.7, 136.7, 146.9, 147.3, 152.4, 170.7, 171.2.
57. 3, 100 MHz): 33.0, 49.6, 52.4, 52.9, 56.0, 59.3, 60.8, 101.1, 102.9, 107.0, 109.4, 110.1, 126.8, 131.3, 136.0, 137.2, 138.1, 147.1, 148.3, 152.8, 169.7, 170.6.
58. Although the yield of this step (65%) is somewhat lower to the calculated global yield of the two separated steps (86%), the success of the pseudo-domino sequence represents an interesting goal from the conceptual (as it validates the feasibility of the principle) as well as practical viewpoint (as it saves a work-up procedure and a purification step).
59. 4, and the solvent was removed in vacuo. The crude product was purified by flash chromatography (cyclohexane/ethyl acetate 8/2) to afford cyclic diester 4 in 65% yield.
60. 3, 100 MHz): 38.3, 49.8, 52.9, 53.4, 56.1, 60.0, 60.8, 102.0, 105.5, 106.6, 108.8, 126.3, 132.7, 137.7, 140.3, 147.9, 153.2, 153.4, 168.3, 169.9, 192.8.