Stereochemical studies. LIII. An asymmetric synthesis of (3S 15S 20R)-yohimbone from L-tryptophan by 1,3-transfer of asymmetry.

Okamura, Kyuya; Yamada, Shunichi

doi:10.1248/cpb.26.2305

Cited by 16 publications

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“…Alumino-and borohydrides 2.1 α-Aminonitriles α-Aminonitriles are transformed into amino derivatives by reductive decyanation using aluminoand borohydrides. 57,[65][66][67][68][69][70][71][72] The mechanism is a S N 1 process with formation of an iminium ion followed by an addition of the hydride ion (Scheme 8). 73 Several facts support this mechanism.…”

Section: Methodsmentioning

confidence: 99%

The reductive decyanation reaction: chemical methods and synthetic applications

Mattalia¹,

Marchi-Delapierre²,

Hazimeh³

et al. 2006

Arkivoc

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Several sequences involving the nitrile group require the removal of this function in a convenient and clean procedure. This transformation, called reductive decyanation, has received much attention over the years. In this review, we describe the chemical methods leading to reductive decyanation as well as the proposed mechanisms. Much of these methodologies proceed with good yields and stereoselectivities allowing their exploitation in organic synthesis.

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Section: Methodsmentioning

confidence: 99%

The reductive decyanation reaction: chemical methods and synthetic applications

Mattalia¹,

Marchi-Delapierre²,

Hazimeh³

et al. 2006

Arkivoc

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show abstract

“…Six alkaloids were isolated. They were, in order of elution from Si gel, yohimbol [1] (3)(4)(5) (1.2% of AM), epi-yohimbol [2} (3)(4)(5) (1.2%), antirhine 13} (6,7) (2.5%), 20-epiantirhine [4} (1.8%), iso-antirhine [5} (8) (2.3%) and 19(S)-hydroxydihydrocorynantheol [6} (0.8%). Compounds 1, 2, 3 and 5 were identified through their spectral and physical properties (ir, uv, nmr, mass spectra, [a}25o).…”

mentioning

confidence: 99%