Taxane Meets Propellane: First Chemical Synthesis of Highly Complex Diterpene Canataxpropellane

Reuß, Franziska; Heretsch, Philipp

doi:10.1002/anie.202002118

Cited by 4 publications

(7 citation statements)

References 20 publications

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“…Very recently, Gaich's group in Konstanz, Germany reported a total synthesis of both racemic and optically active canataxpropellane. 62,63 Their retrosynthetic analysis envisioned generation of the cyclopentane A ring by a pinacol coupling of dialdehyde 123. This dialdehyde can be accessed from 124 by B-ring functionalization at C8 and C5 positions via singlet oxygen cycloaddition.…”

Section: Gaich Synthesis Of (±)-And (-)-Canataxpropellanementioning

confidence: 99%

Recent advances in the synthesis of taxoids: 2015-2020

El‐Mansy¹,

Donaldson²

2021

Arkivoc

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Taxol is a highly oxygenated, polycyclic diterpene first isolated from the bark of the Pacific yew tree. The impressive antitumor activity of this compound led to intense synthetic activity over the past 30 years. The first syntheses were reported more than 25 years ago, and earlier synthetic efforts have been amply reviewed. This review will focus on the literature for the period 2015-2020 including formal and total syntheses of taxol, 1-hydroxytaxinine, taxabaccatin III, and canataxpropellane.

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Section: Gaich Synthesis Of (±)-And (-)-Canataxpropellanementioning

confidence: 99%

Recent advances in the synthesis of taxoids: 2015-2020

El‐Mansy¹,

Donaldson²

2021

Arkivoc

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“…In the endgame, Gaich and coworkers acetylated the secondary alcohol at C-2 selectively and cleaved the acetal via hydrogenation conditions [ 2 ]. The completion of this total synthesis is a milestone in recent synthetic history and was supported by a recent highlight article in Angewandte Chemie by the Heretsch group [ 3 ]. By solving a longtime synthetic challenge, the first total synthesis of canataxpropellane ( 4 ) gives rise to strategies for further complex targets in natural product synthesis ( Scheme 4 ).…”

Section: Synthesismentioning

confidence: 99%

“…Within this review, taxane-derived propellane skeletons and terpenes, as well as terpenoids bearing contiguous asymmetric quaternary carbons, are mentioned to be one of the most exciting future challenges. In 2020, Gaich and coworkers published the first total synthesis of canataxpropellane ( 4 ) [ 2 , 3 ], a previously highlighted future challenge. Waihoensene ( 23 ) was successfully synthesized by Lee and coworkers in 2017 [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

Contiguous Quaternary Carbons: A Selection of Total Syntheses

et al. 2020

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Contiguous quaternary carbons in terpene natural products remain a major challenge in total synthesis. Synthetic strategies to overcome this challenge will be a pivotal prerequisite to the medicinal application of natural products and their analogs or derivatives. In this review, we cover syntheses of natural products that exhibit a dense assembly of quaternary carbons and whose syntheses were uncompleted until recently. While discussing their syntheses, we not only cover the most recent total syntheses but also provide an update on the status quo of modern syntheses of complex natural products. Herein, we review (±)-canataxpropellane, (+)-waihoensene, (–)-illisimonin A and (±)-11-O-debenzoyltashironin as prominent examples of natural products bearing contiguous quaternary carbons.

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“…4 Since then, several research groups have synthesized and studied the properties of different propellanes including heteropropellanes -where the ring structures are not necessarily hydrocarbons. [5][6][7][8][9][10][11] Apart from their strained geometry, propellanes are popular due to their diverse applications in synthetic chemistry ranging from materials to natural products. 5 It is important to note that although the research on propellanes started about 80 years ago, these systems are very common in natural products.…”

Section: Introductionmentioning

confidence: 99%

“…In spite of numerous applications of various propellanes in organic synthesis, there are very few studies focusing on nonlinear optical properties of such compounds. Very recently, some of the present authors have synthesized a heteropropellane-based molecule, 16,20-dinitro- (3,4,8,9)-dibenzo-2,7dioxa-5,10-diaza [4.4.4]propellane (DDDDP) and studied its second-order nonlinear optical (NLO) properties. 11 It was found, using 1064 nm nanosecond laser pulses, that the crystalline powder of DDDDP displays a very high second harmonic generation (SHG) efficiency.…”

Section: Introductionmentioning

confidence: 99%