Asymmetric total synthesis of (−)-conduramine A-1 via a chiral syn,anti-oxazine

Myeong, In‐Soo; Kim, Jin-Seok; Lee, Yong Taek; Kang, Jong-Cheol; Park, Seok‐Hwi; Jung, Changyoung; Ham, Won‐Hun

doi:10.1016/j.tetasy.2016.06.021

Cited by 12 publications

(9 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthesis of conduramines has been achieved via different approaches. 200 Norsikian, Beau, and coworkers reported the synthesis of conduramine A1 292 and C4 296 using a PR of biallylamine and in-house-prepared highly functionalized boronic acids. Starting from multiple protected d -ribofuranose 299 , the boronic acid 300 was prepared and used as the dual aldehyde and boronic component for the lengthy PR.…”

Section: Application In the Synthesis Of Natural Productsmentioning

confidence: 99%

“…Conduramine oligomers, aminocyclohexenetriols in which an amino group is present, are common fragments included in several natural products. The synthesis of conduramines has been achieved via different approaches . Norsikian, Beau, and coworkers reported the synthesis of conduramine A1 292 and C4 296 using a PR of biallylamine and in-house-prepared highly functionalized boronic acids.…”

Section: Application In the Synthesis Of Natural Productsmentioning

confidence: 99%

See 1 more Smart Citation

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

View full text Add to dashboard Cite

The Petasis boron–Mannich reaction, simply referred to as the Petasis reaction, is a powerful multicomponent coupling reaction of a boronic acid, an amine, and a carbonyl derivative. Highly functionalized amines with multiple stereogenic centers can be efficiently accessed via the Petasis reaction with high levels of both diastereoselectivity and enantioselectivity. By drawing attention to examples reported in the past 8 years, this Review demonstrates the breadth of the reactivity and synthetic applications of Petasis reactions in several frontiers: the expansion of the substrate scope in the classic three-component process; nonclassic Petasis reactions with additional components; Petasis-type reactions with noncanonical substrates, mechanism, and products; new asymmetric versions assisted by chiral catalysts; combinations with a secondary or tertiary transformation in a cascade- or sequence-specific manner to access structurally complex, natural-product-like heterocycles; and the synthesis of polyhydroxy alkaloids and biologically interesting molecules.

show abstract

Section: Application In the Synthesis Of Natural Productsmentioning

confidence: 99%

Section: Application In the Synthesis Of Natural Productsmentioning

confidence: 99%

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

View full text Add to dashboard Cite

show abstract

“…Finally, treatment of 30 – 32 with Et 3 SiH in the presence of TFA effected removal of the α-methyl- p -methoxybenzyl fragment to give (−)-conduramine A1 ( 34 ), (−)-conduramine A2 ( 35 ), and (−)-conduramine E2 ( 36 ), in 82%, 79%, and 58% yield, respectively, and in >95:5 dr in each case. The former, (−)-conduramine A1 ( 34 ), has been previously described (as has its antipode), and thus the relative and absolute configurations of 30 were secured. The latter two, (−)-conduramine A2 ( 35 ) and (−)-conduramine E2 ( 36 ), have not been previously described (Scheme ).…”

mentioning

confidence: 70%

Synthesis of (−)-Conduramine A1, (−)-Conduramine A2 and (−)-Conduramine E2 in Six Steps from Cyclohexa-1,4-diene

et al. 2019

View full text Add to dashboard Cite

A method to enable the synthesis of conduramines and their N-substituted derivatives (enantiopure or racemic form) in six steps (five steps for N-substituted derivatives) from cyclohexa-1,4-diene is reported. Key features of this reaction sequence include a preparation of benzene oxide that is amenable to multigram scale, and its efficient ring-opening upon treatment with a primary amine. Epoxidation of the resultant amino alcohols (40% aq HBF4 then m-CPBA) is accompanied by hydrolytic ring-opening in situ to give the corresponding N-substituted conduramine derivatives directly. These may undergo subsequent N-deprotection to give the parent conduramines, as demonstrated by the preparation of enantiopure (−)-conduramine A1, (−)-conduramine A2, and (−)-conduramine E2 (the latter two for the first time). The selectivity of the epoxidation reaction is proposed to be the result of competitive ammonium-directed and hydroxyl-directed epoxidation processes, followed by either direct (SN2-type) or conjugate (SN2′-type) ring-openings of the intermediate epoxides.

show abstract

“…Ham et al, in 2016 27 reported the synthesis of (-)-conduramine A1 from D-serine by using a series of reactions previously described in Scheme 17 21 30 reported the synthesis of N-benzyl conduramine F-1, N-benzyl ent-conduramine E-1, dihydroconduramine F-1 and ent-dihydroconduramine E-1 from D-mannitol. Initially they prepared diol 182 using a described protocol from D-mannitol.…”

Section: Template For Synopen Thiemementioning

confidence: 99%

“…Ham et al, in 2016, 27 reported the synthesis of (-)-conduramine A-1 from D-serine by using the series of reactions shown in Scheme 17[21 (Scheme 21 and Scheme 22). Raghavan et al, in 2016, 28 reported the synthesis of (-)-conduramine B (Scheme 23).…”

Section: Review Synopen Scheme 20 Synthesis Of Conduramine F-4mentioning

confidence: 99%