Research

Numerous organic compounds possessing important bioactivities and novel structures have been found in nature. Our group focuses on the total synthesis of such interesting natural products and their related compounds, and the development of stereoselective synthetic organic reactions.


 Completed Projects

total synthesis of clavilactone D

Keywords: ring-opening/ring-closing metathesis; structure elucidation

1) Takao, K.; Nemoto, R.; Mori, K.; Namba, A.; Yoshida, K.; Ogura, A. Chem. Eur. J. 2017, 23, 3828.


construction of spiroindanes

Keywords: asymmetric catalysis; organocatalysis; spiro compounds

1) Yoshida, K.; Itatsu, Y.; Fujino, Y.; Inoue, H.; Takao, K. Angew. Chem. Int. Ed. 2016, 55, 6734. [Highlighted in Synfacts 2016, 12, 861]


total synthesis of cytosporolide A

Keywords: biomimetic synthesis; hetero-Diels-Alder reaction; o-quinone methide

1) Takao, K.; Noguchi, S.; Sakamoto, S.; Kimura, M.; Yoshida, K.; Tadano, K. J. Am. Chem. Soc. 2015, 137, 15971. [Highlighted in Synfacts 2016, 12, 222]


total synthesis of vibsanin A

Keywords: Barbier-type allylation; intramolecular Nozaki-Hiyama-Kishi reaction; Mitsunobu reaction

1) Takao, K.; Tsunoda, K.; Kurisu, T.; Sakama, A.; Nishimura, Y.; Yoshida, K.; Tadano, K. Org. Lett. 2015, 17, 756.


total synthesis of clavilactones

Keywords: ring-opening/ring-closing metathesis; enantioselective alkynylation

1) Takao, K.; Nanamiya, R.; Fukushima, Y.; Namba, A.; Yoshida, K.; Tadano, K. Org. Lett. 2013, 15, 5582.


total synthesis of bakuchiol

Keywords: asymmetric Claisen rearrangement; all-carbon quaternary stereocenter

1) Takao, K.; Sakamoto, S.; Touati, M. A.; Kusakawa, Y.; Tadano, K. Molecules 2012, 17, 13330.


total synthesis of pestalotiopsin

Keywords: [2+2] cycloaddition; intramolecular Nozaki-Hiyama-Kishi reaction, caryophyllene sesquiterpenoid

1) Takao, K.; Hayakawa, N.; Yamada, R.; Yamaguchi, T.; Saegusa, H.; Uchida, M.; Samejima, S.; Tadano, K. J. Org. Chem. 2009, 74, 6452. [Selected as a Featured Article]
2)  Takao, K.; Hayakawa, N.; Yamada, R.; Yamaguchi, T.; Morita, U.; Kawasaki, S.; Tadano, K. Angew. Chem., Int. Ed. 2008, 47, 3426. [Highlighted in Synfacts 2008, 900]


total synthesis of mycoepoxydiene

Keywords: ring-opening/cross metathesis; ring-closing metathesis; oxygen-bridged cyclooctadiene

1) Takao, K.; Yasui, H.; Yamamoto, S.; Sasaki, D.; Kawasaki, S.; Watanabe, G.; Tadano, K. J. Org. Chem. 2004, 69, 8789.
2) Takao, K.; Watanabe, G.; Yasui, H.; Tadano, K. Org. Lett. 2002, 4, 2941.


total synthesis of cheimonophyllon

Keywords: catalytic asymmetric Mukaiyama aldol reaction; bisabolane sesquiterpenoid

1) Takao, K.; Tsujita, T.; Hara, M.; Tadano, K. J. Org. Chem. 2002, 67, 6690.
2) Takao, K.; Hara, M.; Tsujita, T.; Yoshida, K.; Tadano, K. Tetrahedron Lett. 2001, 42, 4665.


 total synthesis of UPA0044

Keywords: 6-endo cyclization via an epoxy ring opening; p-quinone methide

1) Takao, K.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291.