Total Synthesis of (−)‐Daphenylline

Xu, Bo; Wang, Bingyang; Xun, Wen; Qiu, Fayang G.

doi:10.1002/ange.201902268

Cited by 15 publications

(8 citation statements)

References 80 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“… 21 ( S )-Carvone was employed in stereoselective total synthesis of (−)-daphenylline, an alkaloid present in plants of the Daphniphyllum genus, used in Chinese medicine for their curative properties. 22 …”

Section: Introductionmentioning

confidence: 99%

Description of Chiral Complexes within Functional-Group Symmetry-Adapted Perturbation Theory—The Case of (S/R)-Carvone with Derivatives of (−)-Menthol

2020

View full text Add to dashboard Cite

Symmetry-adapted perturbation theory (SAPT) and functional-group SAPT (F-SAPT) are applied to examine differences in interaction energies of diastereoisomeric complexes of two chiral molecules of natural origin: ( S / R )-carvone with (−)-menthol. The study is extended by including derivatives of menthol with its hydroxy group exchanged by another functional group, thus examining the substituent effect of the interaction and the interaction differences between diastereoisomers. The partitioning of the interaction energy into functional-group components allows one to explain this phenomenon by the mutual cancellation of attractive and repulsive interactions between functional groups. In some cases, one can identify dominant chiral interactions between groups of atoms of carvone and menthol derivatives, while in many other instances, no major interaction can be distinguished and the net chiral difference results from subtle near cancellation of several smaller terms. Our results indicate that the F-SAPT method can be faithfully utilized for such analyses.

show abstract

Section: Introductionmentioning

confidence: 99%

Description of Chiral Complexes within Functional-Group Symmetry-Adapted Perturbation Theory—The Case of (S/R)-Carvone with Derivatives of (−)-Menthol

2020

View full text Add to dashboard Cite

show abstract

“…The structural complexity and biological activities of calyciphylline A‐type alkaloids, which comprise a subfamily of Daphniphyllum alkaloids of around fifty members, have attracted the interest of synthetic researchers in the last sesquidecade. However, the only total syntheses achieved to date are of daphenylline, himalensine A, and longeracinphyllin A, all reported recently ( Figure ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Azabicyclic Building Blocks for Daphniphyllum Alkaloid Intermediates Featuring N‐Trichloroacetyl Enamide 5‐endo‐trig Radical Cyclizations

Jansana

Coussanes

Diaba

et al. 2019

Helvetica Chimica Acta

View full text Add to dashboard Cite

A general procedure is reported for the synthesis of cis ring fused azapolycyclic compounds bearing an all‐carbon quaternary stereocenter at the ring fusion and an adequate functionalization for the assembly of new rings leading to advanced synthetic intermediates for Daphniphyllum alkaloid synthesis. The key carbon−carbon bond‐forming step in this approach is a radical cyclization of an N‐cycloalkenyl trichloroacetamide derivative involving a tetrasubstituted enamide to achieve polyfunctionalized lactams.

show abstract

“…Depending on the taxonomy, the diversified structures of the Daphniphyllum alkaloids can be categorized into 13-35 subfamilies 1,4,7 . To date, about 20 elegant total syntheses of the Daphniphyllum alkaloids, from seven subfamilies, have been reported by the research groups of Heathcock [8][9][10][11][12][13][14][15] , Carreira 16 , Li [17][18][19][20] , Smith 21,22 , Hanessian 23 , Fukuyama/Yokoshima 24 , Zhai 25 , Dixon 26 , Qiu 27 , Gao 28 , and Sarpong 29,30 groups, respectively. Moreover, our group has recently accomplished the asymmetric total syntheses of himalensine A 31 , dapholdhamine B 32 , and caldaphnidine O 33 .…”

mentioning

confidence: 99%

Asymmetric total synthesis of yuzurimine-type Daphniphyllum alkaloid (+)-caldaphnidine J

Guo

Zhang

et al. 2020

Nat Commun

View full text Add to dashboard Cite

Ever since Hirata's report of yuzurimine in 1966, nearly fifty yuzurimine-type alkaloids have been isolated, which formed the largest subfamily of the Daphniphyllum alkaloids. Despite extensive synthetic studies towards this synthetically challenging and biologically intriguing family, no total synthesis of any yuzurimine-type alkaloids has been achieved to date. Here, the first enantioselective total synthesis of (+)-caldaphnidine J, a highly complex yuzuriminetype Daphniphyllum alkaloid, is described. Key transformations of this approach include a highly regioselective Pd-catalyzed hydroformylation, a samarium(II)-mediated pinacol coupling, and a one-pot Swern oxidation/ketene dithioacetal Prins reaction. Our approach paves the way for the synthesis of other yuzurimine-type alkaloids and related natural products.

show abstract

Total Synthesis of (−)‐Daphenylline

Cited by 15 publications

References 80 publications

Description of Chiral Complexes within Functional-Group Symmetry-Adapted Perturbation Theory—The Case of (S/R)-Carvone with Derivatives of (−)-Menthol

Description of Chiral Complexes within Functional-Group Symmetry-Adapted Perturbation Theory—The Case of (S/R)-Carvone with Derivatives of (−)-Menthol

Synthesis of Azabicyclic Building Blocks for Daphniphyllum Alkaloid Intermediates Featuring N‐Trichloroacetyl Enamide 5‐endo‐trig Radical Cyclizations

Asymmetric total synthesis of yuzurimine-type Daphniphyllum alkaloid (+)-caldaphnidine J

Contact Info

Product

Resources

About