Totalsynthese von (+)‐Crotogoudin

Breitler, Simon; Carreira, Erick M.

doi:10.1002/ange.201305822

Angewandte Chemie

2013

DOI: 10.1002/ange.201305822

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Totalsynthese von (+)‐Crotogoudin

Simon Breitler

Erick M. Carreira

Abstract: Ein Ring für einen Ring: Die erste Totalsynthese von Crotogoudin, einem 3,4‐seco‐Atisan‐Diterpen, wird beschrieben. Der asymmetrische Zugang zum Bicyclo[2.2.2]octan‐Kern gelang durch Desymmetrisierung eines meso‐Diketons mit Backhefe (LG=Abgangsgruppe, EWG=elektronenziehende Gruppe), und eine SmI2‐induzierte radikalische Cyclopropanöffnung/Ringschluss/Eliminierungs‐Kaskade baute das tetracyclische Grundgerüst von (+)‐Crotogoudin auf. Die Synthese führte zur Revision der publizierten optischen Drehwerte des Nat… Show more

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Cited by 18 publications

References 61 publications

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Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)‐Pallambins A and B

Ebner

Carreira

2015

Angewandte Chemie

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The first total syntheses of pallambins Aa nd Ba re enabled by the use of pentafulvene in an unprecedented Diels-Alder reaction. After elaboration of the adduct through chemoselective cyclopropanation, strategic CÀHi nsertion affords the dense tetracyclic core of the natural products.1 ,3-Dipolar cycloaddition and palladium(II)-catalyzed alkoxycarbonylation were leveraged for the construction of the hexacyclic scaffold en route to both natural products.

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Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)‐Pallambins A and B

Ebner

Carreira

2015

Angewandte Chemie

Self Cite

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Collective Total Syntheses of Atisane‐Type Diterpenes and Atisine‐Type Diterpenoid Alkaloids: (±)‐Spiramilactone B, (±)‐Spiraminol, (±)‐Dihydroajaconine, and (±)‐Spiramines C and D

et al. 2015

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The first total syntheses of the architecturally complex atisane‐type diterpenes and biogenetically related atisine‐type diterpenoid alkaloids (±)‐spiramilactone B, (±)‐spiraminol, (±)‐dihydroajaconine, and (±)‐spiramines C and D are reported. Highlights of the synthesis include a late‐stage biomimetic transformation of spiramilactone B, a facile formal lactone migration from the pentacyclic skeleton of spiramilactone E, a highly efficient and diastereoselective 1,7‐enyne cycloisomerization to construct the functionalized tetracyclic atisane skeleton, and a tandem retro‐Diels–Alder/intramolecular Diels–Alder sequence to achieve the tricyclo[6.2.2.0] ring system.

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Scalable Total Synthesis of rac‐Jungermannenones B and C

Liu

Cai

et al. 2016

Angewandte Chemie

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Reported is the first scalable synthesis of racjungermannenones Ba nd Cs tarting from the commercially available and inexpensive geraniol in 10 and 9s teps,r espectively.T he unique jungermannenone framework is rapidly assembled by an unprecedented regioselective 1,6-dienyne reductive cyclization reaction whichp roceeds through av inyl radical cyclization/allylic radical isomerization mechanism. DFT calculations explain the high regioselectivity observed in the 1,6-dienyne reductive radical cyclization.

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Totalsynthese von (+)‐Crotogoudin

Cited by 18 publications

References 61 publications

Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)‐Pallambins A and B

Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)‐Pallambins A and B

Collective Total Syntheses of Atisane‐Type Diterpenes and Atisine‐Type Diterpenoid Alkaloids: (±)‐Spiramilactone B, (±)‐Spiraminol, (±)‐Dihydroajaconine, and (±)‐Spiramines C and D

Scalable Total Synthesis of rac‐Jungermannenones B and C

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