TY - JOUR

T1 - Total Synthesis and Structure Revision of Halioxepine

AU - Poock, Caroline

AU - Kalesse, Markus

N1 - Funding Information: We are very grateful to Prof. J. Tanaka (University of the Ryukyus) for providing NMR-Spectra of authentic halioxepine. We also thank Prof. J. Rodriguez (Universidade da Coru?a) for cooperation with respect to NMR-spectra. We thank Dr. J. Fohrer, M. Rettstadt and D. K?rtje for detailed NMR analysis and A. Schulz and R. Reichel for mass spectra. In terms of preparation of the manuscript we thank Alina Eggert, Giada Tedesco, Alexandru-Adrian Sara and Daniel L?cke. Open access funding enabled and organized by Projekt DEAL.

PY - 2021/1/21

Y1 - 2021/1/21

N2 - The first total synthesis of halioxepine is accomplished using a 1,4-addition for constructing the quaternary center at C10 and a halo etherification for the generation of the tertiary ether at C7. The correct structure of halioxepine was determined by assembling different enantiomeric building blocks and by changing the relative configuration between C10 and C15.

AB - The first total synthesis of halioxepine is accomplished using a 1,4-addition for constructing the quaternary center at C10 and a halo etherification for the generation of the tertiary ether at C7. The correct structure of halioxepine was determined by assembling different enantiomeric building blocks and by changing the relative configuration between C10 and C15.

KW - halo etherification

KW - natural product synthesis

KW - quaternary stereocenter

KW - structure elucidation

KW - terpenoids

UR - http://www.scopus.com/inward/record.url?scp=85097881614&partnerID=8YFLogxK

U2 - 10.1002/chem.202004847

DO - 10.1002/chem.202004847

M3 - Article

C2 - 33215739

AN - SCOPUS:85097881614

VL - 27

SP - 1615

EP - 1619

JO - Chemistry - a European journal

JF - Chemistry - a European journal

SN - 0947-6539

IS - 5

ER -