Semipinacol rearrangement in natural product synthesis

ZL Song, CA Fan, YQ Tu - Chemical reviews, 2011 - ACS Publications
The pinacol rearrangement1 is a well-known reaction. It refers to the acid-catalyzed
transformation of 1, 2-diols to ketones or aldehydes by 1, 2-migration of a CÀC or CÀH bond …

Recent advances in the semi-pinacol rearrangement of α-hydroxy epoxides and related compounds

TJ Snape - Chemical Society Reviews, 2007 - pubs.rsc.org
The semi-pinacol rearrangement is fast becoming an extremely reliable reaction in organic
synthesis allowing the rapid construction of relatively complex stereodefined products in …

Total syntheses of (+)-tedanolide and (+)-13-deoxytedanolide

JR Dunetz, LD Julian, JS Newcom… - Journal of the American …, 2008 - ACS Publications
Convergent total syntheses of the potent cytotoxins (+)-tedanolide (1) and (+)-13-
deoxytedanolide (2) are described. The carbon framework of these compounds was …

Direct methods for stereoselective polypropionate synthesis: a survey

J Li, D Menche - Synthesis, 2009 - thieme-connect.com
Polypropionates are key subunits in structurally diverse polyketide natural products and
pharmaceuticals, rendering their synthesis an objective of high priority in synthetic organic …

A synthetic approach toward nitiol: Construction of two 1, 22-dihydroxynitianes

MS Wilson, JCS Woo, GR Dake - The Journal of Organic …, 2006 - ACS Publications
Synthetic work toward the total synthesis of nitiol has culminated in the construction of two
epimeric hydroxylated derivatives, the 1, 22-dihydroxynitianes. Key stereodefining steps in …

Asymmetric Synthesis of anti-Aldol Segments via a Nonaldol Route: Synthetic Applications to Statines and (−)-Tetrahydrolipstatin

AK Ghosh, K Shurrush, S Kulkarni - The Journal of organic …, 2009 - ACS Publications
An asymmetric synthesis of anti-aldol segments via a nonaldol route is described. The
strategy involves a highly diastereoselective synthesis of functionalized tetrahydrofuran …

The Total Synthesis of (+)‐Tedanolide—A Macrocyclic Polyketide from Marine Sponge Tedania ignis

G Ehrlich, J Hassfeld, U Eggert… - Chemistry–A European …, 2008 - Wiley Online Library
Tedanolide, which was isolated by Schmitz in 1984 from the marine sponge Tedania ignis,
is a highly cytotoxic macrolide leading to strong growth inhibition of P338 tumor cells in …

Construction of azaspirocyclic ketones through α-hydroxyiminium ion or α-siloxy epoxide semipinacol rearrangements

MDB Fenster, BO Patrick, GR Dake - Organic Letters, 2001 - ACS Publications
Construction of Azaspirocyclic Ketones through α-Hydroxyiminium Ion or α-Siloxy Epoxide
Semipinacol Rearrangements | Organic Letters ACS ACS Publications C&EN CAS Find my …

Investigations of α-Siloxy− Epoxide Ring Expansions Forming 1-Azaspirocyclic Ketones

GR Dake, MDB Fenster, M Fleury… - The Journal of Organic …, 2004 - ACS Publications
The construction of 1-azaspirocyclic cycloalkanones using a siloxy− epoxide semipinacol
ring expansion process was examined. Functionalized 1-azaspiro [5.5] undecan-7-ones (1 …

Total synthesis of (+)-asteltoxin

KD Eom, JV Raman, H Kim, JK Cha - Journal of the American …, 2003 - ACS Publications
A convergent synthesis of (+)-asteltoxin (1) has been achieved by the Horner− Emmons
olefination of bis (tetrahydrofuran) aldehyde 53 and α-pyrone phosphonate 5. A key step …