The 25th ISHC Congress–Santa Barbara CA Aug 23-28, 2015
!
Important notes:
You MUST use this template. If you don’t use it your abstract WILL be rejected.
Do NOT enter author and institution information on this form. You will be able to
enter this information online when you submit the abstract.
Do NOT write outside the boxes. Any text or images outside the boxes will be
deleted.
Do NOT alter this form by deleting parts of it or adding new boxes. Simply enter
your information into the boxes. The form will be automatically processed – if you
alter it your submission will not be processed correctly.
An un-sized >10point font is highly recommended for Chemdraw graphics
Save this file in .doc or .docx format.
Title:
SYNTHESIS OF NATURAL PRODUCTS CONTAINING SPIROKETALS
Abstract: (Your abstract must use Normal style and must fit into the box. Do not enter author details)
Natural products have long been regarded as “Nature’s medicine chest” providing
invaluable platforms for developing front-line drugs. The chemical structures of natural
products have evolved over several millennia for a specific biochemical purpose and their
molecular frameworks can be considered “privileged scaffolds.” This lecture will showcase
how natural products that contain intricate spiroketal scaffolds can be synthesized thus
providing a platform to develop novel anticancer and anti-obesity agents.
The virgatolides are a family of natural products containing a rare benzannulated 6,6spiroketal moiety isolated in 2011 from Pestalotiopsis virgatula.1 Virgatolides A-C exhibit
cytotoxicity against HeLa cells (IC50 ~ 20 µM). The first synthesis2 of virgatolide B is
described. Phorbaketal A and alotaketal A are two pseudoenantiomeric natural products,
containing a unique spiro-sesterterpenoid core structure.3,4 Phorbaketal A possesses
moderate cytotoxicity against a range of cancer cell lines, as well as exhibiting osteoblast
and mast cell differentiation activity and inhibition of fatty acid synthesis in the liver.
Additionally, alotaketal A activates the cAMP signalling pathway at nanomolar
concentrations. Our efforts directed towards the enantioselective syntheses of phorbaketal
A and alotaketal A will be described.5
OH
OH
O
Me
HO
O
H
O
O
Me
O
H
O
O
HO
virgatolide B
phorbaketal A
1. Li, J.; Li, L.; Si, Y.; Jiang, X.; Guo, L.; Che, Y. Org. Lett. 2011, 13, 2670.
2. Hume, P. A.; Furkert, D.P.; Brimble, M.A. Org. Lett. 2013, 15, 4588.
3. Rho, J.-R.; Hwang, B.S.; Sim, C.J.; Joung, S.; Lee, H.-Y.; Kim, H.-J. Org. Lett. 2009, 11, 5590.
4. Forestieri, R.; Merchant, C.E.; Matainaho, T.; Kieffer, T.J.; Andersen, R.J. Org. Lett. 2009, 11, 5166.
5. Hubert, J.G.; Furkert, D.P.; Brimble, M.A. J. Org. Chem. 2015, 80, 2231; J. Org. Chem. 2015, 80, 2715.