Enantioselective synthesis of altohyrtin C (spongistatin 2): synthesis of the AB‐and CD‐spiroketal subunits

DA Evans, PJ Coleman, LC Dias - … Chemie International Edition …, 1997 - Wiley Online Library
… we describe the synthesis of the C, C,, AB-spiroketal and C,,-… CD-spiroketal altohyrtin
subunits, which will be joined … Multiple deprotection and spiroketalization of this substrate was …

Enantioselective total synthesis of altohyrtin C (spongistatin 2)

DA Evans, BW Trotter, PJ Coleman, B Côté, LC Dias… - Tetrahedron, 1999 - Elsevier
… This is particularly evident in systems containing a hydroxyl group and a spiro CO bond in
a … spongistatin 2 and altohyrtin C are identical compounds and speculate that the altohyrtin

Stereocontrolled Total Synthesis of (+)‐Altohyrtin A/Spongistatin 1

I Paterson, DYK Chen, MJ Coster… - Angewandte Chemie …, 2001 - Wiley Online Library
… highly stereocontrolled total synthesis of the most active congener, altohyrtin A/spongistatin
1 (… Throughout our synthesis, asymmetric boron aldol reactions of ketones are exploited as a …

[图书][B] Synthesis of the C1-C28 subunit of altohyrtin A (spongistatin 1): The AB and CD spiroketal moieties

MM Claffey - 1998 - search.proquest.com
… that spongistatin 2 and altohyrtin C are identical compounds. The resulting implication was
that the altohyrtin and spongistatin … He confirmed the accessibility of the spiro compound 101 …

Enantioselective synthesis of structurally intricate and complementary polyoxygenated building blocks of Spongistatin 1 (Altohyrtin A)

A Braun, IH Cho, S Ciblat, D Clyne… - Collection of …, 2009 - cccc.uochb.cas.cz
… potent antineoplastic macrocyclic lactone spongistatin 1 (1a) … subsequently recognized to be
identical to spongistatin 4 (1b)10. … Although several macrolide antibiotics featuring one spiro

Synthesis of Cytotoxic Marine Macrolides: An Aldol-Based Approach to Spongistatin 1 (Altohyrtin A)

I Paterson, KR Gibson, LE Keown, RD Norcross… - … in Organic Synthesis, 1999 - Springer
… 1, our retrosynthetic analysis for spongistatin 1 (1) is based … the CIS-CI6 bond linking the two
spiro acetal ring systems. We … for achieving remote asymmetric induction in the synthesis of …

[图书][B] … cyclization: Synthetic studies toward the CD subunit of spongistatin I (altohyrtin A), and, Studies toward the kinetic resolution of lactols using a ruthenium (II) …

LR Takaoka - 2004 - search.proquest.com
synthesis of the CD subunit of spongistatin 1 (altohyrtin A). A … Successful preparation of
the [4.5]-spiro-THP system … reductive cyclization of allylic ethers for the formation of spiro-THP …

[HTML][HTML] Recent synthetic approaches toward non-anomeric spiroketals in natural products

S Favre, P Vogel, S Gerber-Lemaire - Molecules, 2008 - mdpi.com
… of such structures assumed that the configuration of the spiro … on the total synthesis of
spongistatin 1/altohyrtin A in 2001 [25]… developed for the asymmetric synthesis of C 15 polyketides …

Short Diastereoselective Synthesis of the C1–C13 (AB Spiroacetal) and C17–C28 Fragments (CD Spiroacetal) of Spongistatin 1 and 2 through Double Chain …

CL Flowers, P Vogel - Chemistry–A European Journal, 2010 - Wiley Online Library
synthesis of the C29–C51 fragments of spongistatin 114 and has developed a noniterative
approach to the asymmetric synthesis of … of AB15 and CD16 spiroacetals of spongistatin 1–3 …

Studies in marine macrolide synthesis: Synthesis of a C16 C28 subunit of spongistatin 1 (altohyrtin A) incorporating the CD-spiroacetal moiety

I Paterson, DJ Wallace, KR Gibson - Tetrahedron letters, 1997 - Elsevier
The C 16 C 28 ketone 3, containing the CD-spiroacetal of spongistatin 1 (1), was prepared
in … Both thermodynamic and kinetic conditions were explored for controlling the CD-acetal …