Nakiterpiosin

Gao, Shuanhu; Chen, Chuo

doi:10.1007/978-3-642-34065-9_2

Total Synthesis of Natural Products 2012

DOI: 10.1007/978-3-642-34065-9_2

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Nakiterpiosin

Shuanhu Gao

Chuo Chen

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Cited by 2 publications

References 89 publications

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Lewis Acid Mediated Nazarov Cyclization as a Convergent and Enantioselective Entry to C‐nor‐D‐homo‐Steroids

Krieger

Smeilus

Schackow

et al. 2017

Chemistry A European J

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A straightforward synthesis of C-nor-D-homo steroids starting from (+)-Wieland-Miescher ketone is reported. This convergent synthetic strategy utilizes a scalable diastereoselective Nazarov cyclization of functionalized chiral aryl vinyl ketones, allowing for further functionalization. The ability to conduct this key transformation on a multi-gram scale paves the way for the synthesis of a variety of completely new C-nor-D-homo steroids, without the need of a classic steran steroid rearrangement or achiral linear reaction sequences.

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Lewis Acid Mediated Nazarov Cyclization as a Convergent and Enantioselective Entry to C‐nor‐D‐homo‐Steroids

Krieger

Smeilus

Schackow

et al. 2017

Chemistry A European J

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Enantioselective Total Synthesis of (+)-Heilonine

Cassaidy

Rawal

2021

J. Am. Chem. Soc.

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Chemical transformations that rapidly and efficiently construct a high level of molecular complexity in a single step are perhaps the most valuable in total synthesis. Among such transformations is the transition metal catalyzed [2 + 2 + 2] cycloisomerization reaction, which forges three new C–C bonds and one or more rings in a single synthetic operation. We report here a strategy that leverages this transformation to open de novo access to the Veratrum family of alkaloids. The highly convergent approach described herein includes (i) the enantioselective synthesis of a diyne fragment containing the steroidal A/B rings, (ii) the asymmetric synthesis of a propargyl-substituted piperidinone (F ring) unit, (iii) the high-yielding union of the above fragments, and (iv) the intramolecular [2 + 2 + 2] cycloisomerization reaction of the resulting carbon framework to construct in a single step the remaining three rings (C/D/E) of the hexacyclic cevanine skeleton. Efficient late-stage maneuvers culminated in the first total synthesis of heilonine (1), achieved in 21 steps starting from ethyl vinyl ketone.

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Nakiterpiosin

Cited by 2 publications

References 89 publications

Lewis Acid Mediated Nazarov Cyclization as a Convergent and Enantioselective Entry to C‐nor‐D‐homo‐Steroids

Lewis Acid Mediated Nazarov Cyclization as a Convergent and Enantioselective Entry to C‐nor‐D‐homo‐Steroids

Enantioselective Total Synthesis of (+)-Heilonine

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