Total synthesis of (-)-pseudopterosin A

Broka, Chris A.; Chan, S.; Peterson, Barry C.

doi:10.1021/jo00242a053

Cited by 71 publications

(34 citation statements)

References 2 publications

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“…The silyl ketene acetal derivative of lactone 37 was generated by sequential treatment with lithium diisopropylamide (LDA) and trimethylsilyl chloride (TMSCl). Protonation of this intermediate with acetic acid at 0 °C took place with high stereoselectivity from the less-hindered face 51. Reduction of the crude lactone product with LiAlH 4 then delivered diol 36b in 78% overall yield after recrystallization 51…”

Section: Resultsmentioning

confidence: 99%

A Unified Strategy for Enantioselective Total Synthesis of Cladiellin and Briarellin Diterpenes: Total Synthesis of Briarellins E and F and the Putative Structure of Alcyonin and Revision of Its Structure Assignment

2009

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Enantioselective total syntheses of briarellin E (12) and briarellin F (13), as well as the structure originally proposed for the cladiellin diterpene alcyonin (10), have been realized. Comparison of the spectral data for synthetic 10, natural alcyonin, cladiellisin (33), and cladiellaperoxide (34), as well as chemical transformations of 10 and natural alcyonin, suggest that the structure of this coral metabolite is allylic peroxide 11. The unified approach detailed herein can be used to access both C4-deoxygenated and C4-oxygenated cladiellins and briarellins. The central step in these syntheses is acid-promoted condensation of (Z)-α,β-unsaturated aldehydes 17 with cyclohexadienyl diols 18, to form intermediates 16 incorporating the hexahydroisobenzofuran core and five stereocenters of these marine diterpenes (Scheme 1).

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Section: Resultsmentioning

confidence: 99%

A Unified Strategy for Enantioselective Total Synthesis of Cladiellin and Briarellin Diterpenes: Total Synthesis of Briarellins E and F and the Putative Structure of Alcyonin and Revision of Its Structure Assignment

2009

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“…In a typical experiment, (3) was treated with 5 eq. of MeLi in tetrahydrofuran at 195 K for 5 min to generate the a-oxy organolithium species (Broka & Shen, 1989;Broka, Lee & Shen, 1988). Upon warming to 273 K and stirring for 2 h, the bicyclo[5.3.0] tetrahydrofuran (4) was produced in 85% yield.…”

Section: Methodsmentioning

confidence: 99%

A Highly Substituted trans-Fused Bicyclo[5.3.0]decene

Kumanovic¹,

Lautens²,

Lough³

1995

Acta Crystallogr C

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“…2B). 50 Their synthesis began with commercially available (S)-(−)-limonene (16), which was transformed into the precursor for the first annulation event, silyl enol ether 17, in 17 steps. 51 This compound, obtained as a diastereomeric mixture, was united with diene 18 in a one-pot [3+3] annulation, comprising an inter-followed by intramolecular Mukaiyama aldol reaction.…”

Section: Pseudopterosin a Broka 1988mentioning

confidence: 99%